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Diisopropylethylamine → HCID 44137940, compound

HRID 2076211
Notes
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Reaction equation

HRID 2076211 reaction equation
[F:1][C:2]1[C:3]2[N:4]([CH:20]=[N:21][CH:22]=2)[C:5]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([I:18])=[CH:14][C:13]=2[F:19])=[C:6]([C:8](O)=[O:9])[CH:7]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.Cl.[OH:57][C@@H:58]([CH3:62])[CH2:59][O:60][NH-:61]>C1COCC1>[OH:57][C@@H:58]([CH3:62])[CH2:59][O:60][NH:61][C:8]([C:6]1[CH:7]=[C:2]([F:1])[C:3]2[N:4]([CH:20]=[N:21][CH:22]=2)[C:5]=1[NH:11][C:12]1[CH:17]=[CH:16][C:15]([I:18])=[CH:14][C:13]=1[F:19])=[O:9]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59140183HCID 59140183, compoundHCID 86637726(S)-2-hydroxy-propoxy-amide hydrochloride

Product 1

HCID 44137940HCID 44137940, compoundYield 11.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 8-fluoro-5-(2-fluoro-4-iodo-phenylamino)-imidazo[1,5-a]pyridine-6-carboxylic acid (100 mg, 0.23 mmol), HATU (130 mg, 0.34 mmol), DIPEA (0.06 mL, 0.34 mmol) and (S)-2-hydroxy-propoxy-amide hydrochloride (44 mg, 0.34 mmol) in THF (1 mL) was stirred at room temperature for 18 hours. The reaction mixture was partitioned between ethyl acetate (5 mL) and 1M HCl, the organic layer was isolated and washed with saturated aqueous NaHCO3 (2×5 mL) and brine (2×5 mL), dried over Na2SO4, filtered and concentrated in vacuo. The resultant residue was subjected to reverse-phase preparative HPLC (Gemini 5 micron C18 250×21.20 mm column, 0.1% formic acid, gradient acetonitrile/water, 5 to 98%, ramp time 20 minutes) to afford the title compound as a yellow solid (13 mg, 8%). LCMS (method A): RT=8.13 min, [M+H]+=489. 1H NMR (DMSO-d6):11.51 (1H, broad), 8.95 (1H, broad), 8.25 (1H, s), 7.60 (1H, s), 7.55 (1H, d, J=10.7 Hz), 7.27 (1H, d, J=8.4 Hz), 6.82 (1H, d, J=11.1 Hz), 6.32 (1H, t, J=8.8 Hz), 4.66 (1H, broad), 3.64 (1H, m), 3.43 (2H, d, J=5.8 Hz), 0.94 (3H, d, J=6.3 Hz).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate (5 mL) and 1M HCl
  2. customthe organic layer was isolated
  3. washwashed with saturated aqueous NaHCO3 (2×5 mL) and brine (2×5 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customwas subjected to reverse-phase preparative HPLC (Gemini 5 micron C18 250×21.20 mm column, 0.1% formic acid, gradient acetonitrile/water, 5 to 98%, ramp time 20 minutes)

Sources & evidence

ORD record
ord-b612a09f36f14fb88610d259e2c938ce
Source dataset
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07923456B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes