Ammonia → 1-{[2-(1,1-Dimethylpropyl)-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}-1H-pyrazole-4-carboxamide

HRID 1435468Notes

Reaction equation

HRID 1435468 reaction equation
CC[N:3](C(C)C)C(C)C.[CH3:10][C:11]([C:15]1[N:19]([CH2:20][CH:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[C:18]2[CH:27]=[CH:28][C:29]([S:31]([N:34]3[CH:38]=[C:37]([C:39]([OH:41])=O)[CH:36]=[N:35]3)(=[O:33])=[O:32])=[CH:30][C:17]=2[N:16]=1)([CH3:14])[CH2:12][CH3:13].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.N>CN(C=O)C>[CH3:14][C:11]([C:15]1[N:19]([CH2:20][CH:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[C:18]2[CH:27]=[CH:28][C:29]([S:31]([N:34]3[CH:38]=[C:37]([C:39]([NH2:3])=[O:41])[CH:36]=[N:35]3)(=[O:32])=[O:33])=[CH:30][C:17]=2[N:16]=1)([CH3:10])[CH2:12][CH3:13]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 579373031-(2-tert-pentyl-1-((tetrahydro-2H-pyran-4-yl)methyl)-1H-benzo[d]imidazol-5-ylsulfonyl)-1H-pyrazole-4-carboxylic acid

Product 1

HCID 236606601-{[2-(1,1-Dimethylpropyl)-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}-1H-pyrazole-4-carboxamideYield 18.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following the same procedure in Example 24, Step A, using DIPEA (105 uL, 78 mg, 0.60 mmol), 1-{[2-(1,1-dimethylpropyl)-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}-1H-pyrazole-4-carboxylic acid (0.20 mmol), HATU (114 mg, 0.30 mmol) and saturated ammonia in DMF (5 mL). The crude product was purified by MPLC using CH2Cl2/MeOH (20:1) on silica gel to give 17 mg (18%) of a white solid as the title compound. 1H NMR (400 MHz, METHANOL-D4) δ 0.78 (t, J=7.52 Hz, 3 H), 1.41-1.57 (m, 4 H), 1.59 (s, 6 H), 1.95 (q, J=7.42 Hz, 2 H), 2.20-2.37 (m, 1 H), 3.22-3.38 (m, 2 H), 3.90 (dd, J=11.82, 3.22 Hz, 2 H), 4.42 (d, J=7.42 Hz, 2 H), 7.94 (d, J=8.8 Hz, 1 H), 8.01 (dd, J=8.8, 1.8 Hz, 1 H), 8.05 (s, 1 H), 8.36 (d, J=1.56 Hz, 1 H), 8.79 (d, J=0.59 Hz, 1 H); MS (ESI) (M+H)+=460.3.

Workup

  1. customThe crude product was purified by MPLC

Sources & evidence

ORD record
ord-5a8ac58465a5407bbd98d795e3513fa0
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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