Diisopropylethylamine → HCID 178522291, compound

HRID 2168229Notes

Reaction equation

HRID 2168229 reaction equation
[N:1]1[C:6]2[NH:7][CH:8]=[CH:9][C:5]=2[C:4]([N:10]2[CH2:15][CH2:14][CH:13]([NH2:16])[CH2:12][CH2:11]2)=[N:3][CH:2]=1.[N:17]1[CH:22]=[CH:21][C:20]([C:23](O)=[O:24])=[CH:19][N:18]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=NC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C>[NH:1]1[C:6]2=[N:7][CH:8]=[CH:9][C:5]2=[C:4]([N:10]2[CH2:11][CH2:12][CH:13]([NH:16][C:23]([C:20]3[CH:21]=[CH:22][N:17]=[N:18][CH:19]=3)=[O:24])[CH2:14][CH2:15]2)[N:3]=[CH:2]1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 181649HOAtHCID 2761046Pyridazine-4-carboxylic AcidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11564772HCID 11564772, compound

Product 1

HCID 178522291HCID 178522291, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-4-piperidinamine D2 (100 mg), 4-pyridazinecarboxylic acid (57.1 mg, 0.460 mmol), HATU (210 mg, 0.552 mmol) and HOAt (37.60 mg, 0.276 mmol) in DMF (2.3 mL) was added DIPEA (386 μL, 2.209 mmol). The reaction mixture was stirred at room temperature for 2 hours then the solvent was removed in vacuo. The crude mixture was purified by MDAP using a formic acid method to afford E13 (44 mg), 1H NMR (d6-DMSO) δ 11.70 (1H, brs), 9.55 (1H, s), 9.42 (1H, d), 8.80 (1H, d), 8.17 (1H, s), 8.0 (1H, d), 7.20 (1H, d), 6.60 (1H, d), 4.70 (2H, dt), 4.15 (1H, m), 3.25 (2H, dt), 1.90 (2H, m), 1.60 (2H, m), MS(ES+) 324 [M+H]+.

Workup

  1. customthe solvent was removed in vacuo
  2. customThe crude mixture was purified by MDAP
  3. customto afford E13 (44 mg), 1H NMR (d6-DMSO) δ 11.70 (1H, brs), 9.55 (1H, s), 9.42 (1H, d), 8.80 (1H, d), 8.17 (1H, s), 8.0 (1H, d), 7.20 (1H, d), 6.60 (1H, d), 4.70 (2H, dt), 4.15 (1H, m), 3.25 (2H, dt), 1.90 (2H, m), 1.60 (2H, m), MS(ES+) 324 [M+H]+

Sources & evidence

ORD record
ord-a7a7fce0dc9948a3818996b30dd87c2d
Source dataset
uspto-grants-2015_06
Patent number
US09045485B2

Reaction notes

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