Hydrochloric Acid → HCID 86703176, compound

HRID 2204375Notes

Reaction equation

HRID 2204375 reaction equation
[Cl:1][C:2]1[C:3]([F:40])=[C:4]([N:8]2[C:15](=[O:16])[C:14]3[CH:13]=[C:12]([C:17]4[CH:18]=[C:19]([CH2:25][C:26]([OH:28])=O)[CH:20]=[N:21][C:22]=4[O:23][CH3:24])[N:11]([CH:29]([CH3:31])[CH3:30])[C:10]=3[CH:9]2[C:32]2[CH:37]=[CH:36][C:35]([C:38]#[N:39])=[CH:34][CH:33]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:41][N:42](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1.CN.Cl>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[C:3]([F:40])=[C:4]([N:8]2[C:15](=[O:16])[C:14]3[CH:13]=[C:12]([C:17]4[CH:18]=[C:19]([CH2:25][C:26]([NH:42][CH3:41])=[O:28])[CH:20]=[N:21][C:22]=4[O:23][CH3:24])[N:11]([CH:29]([CH3:31])[CH3:30])[C:10]=3[CH:9]2[C:32]2[CH:33]=[CH:34][C:35]([C:38]#[N:39])=[CH:36][CH:37]=2)[CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 79724-MethylmorpholineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86703177HCID 86703177, compound

Product 1

HCID 86703176HCID 86703176, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of {5-[5-(3-chloro-2-fluoro-phenyl)-6-(4-cyano-phenyl)-1-isopropyl-4-oxo-1,4,5,6-tetrahydro-pyrrolo[3,4-b]pyrrol-2-yl]-6-methoxy-pyridin-3-yl}-acetic acid (Step 85.1) (0.054 mmol), HATU (0.161 mmol), NMM (0.215 mmol) and methylamine.HCl (0.081 mmol) in DMF (0.5 mL) at rt was stirred for 2 h. The reaction mixture was diluted with EtOAc and successively washed with a saturated aqueous solution of NaHCO3 (2×) and brine, dried (MgSO4), filtered and concentrated. The residue was purified using a silica gel column to afford the title compound as a white solid. tR: 4.96 min (HPLC 4); ESI-MS: tR=1.02 min, [M+H]+ 572/574 (LC-MS 1).

Workup

  1. washsuccessively washed with a saturated aqueous solution of NaHCO3 (2×) and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified

Sources & evidence

ORD record
ord-2b28a9dd0a3c489faf85c74d45da5c2e
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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