Diisopropylethylamine → 1-{[2-tert-Butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}-N-methyl-1H-pyrrole-3-carboxamide

HRID 1435452Notes

Reaction equation

HRID 1435452 reaction equation
C[CH2:2][N:3](C(C)C)C(C)C.[C:10]([C:14]1[N:18]([CH2:19][CH:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[C:17]2[CH:26]=[CH:27][C:28]([S:30]([N:33]3[CH:37]=[CH:36][C:35]([C:38]([OH:40])=O)=[CH:34]3)(=[O:32])=[O:31])=[CH:29][C:16]=2[N:15]=1)([CH3:13])([CH3:12])[CH3:11].Cl.CN.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[C:10]([C:14]1[N:18]([CH2:19][CH:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[C:17]2[CH:26]=[CH:27][C:28]([S:30]([N:33]3[CH:37]=[CH:36][C:35]([C:38]([NH:3][CH3:2])=[O:40])=[CH:34]3)(=[O:32])=[O:31])=[CH:29][C:16]=2[N:15]=1)([CH3:13])([CH3:12])[CH3:11]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 6364545Methylamine hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 579373191-{[2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}-1H-pyrrole-3-carboxylic acid

Product 1

HCID 236603081-{[2-tert-Butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}-N-methyl-1H-pyrrole-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following the same procedure in Example 33, step A, using DIPEA (0.37 mL, 274 mg, 2.2 mmol), 1-{[2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}-1H-pyrrole-3-carboxylic acid (0.12 mmol) (see the step B in example 33 for preparation), methylamine hydrochloride (100 mg, 1.45 mmol) and HATU (150 mg, 0.40 mmol) in DMF (5 mL). The crude product was purified by MPLC using Hex/EtOAc (3:7) on silica gel to 25 mg (45%) of a white solid as the title compound. 1H NMR (400 MHz, METHANOL-D4) δ 1.41-1.58 (m, 4 H), 1.61 (s, 9 H), 2.21-2.41 (m, 1 H), 2.79 (s, 3 H), 3.23-3.35 (m, 2 H), 3.83-3.96 (m, 2 H), 4.44 (d, J=7.62 Hz, 2 H), 6.63 (dd, J=3.32, 1.76 Hz, 1 H), 7.30 (dd, J=3.32, 2.34 Hz, 1H), 7.75-7.80 (m, 1 H), 7.95 (d, J=8.7 Hz, 1 H), 7.98 (dd, J=8.7, 1.5 Hz, 1 H), 8.27 (d, J=0.98 Hz, 1 H); MS (ESI) (M+H)+=458.8; Anal. Calcd for C23H30N4O4S+1.50 TFA (629.62): C, 49.60; H, 5.04; N, 8.90. Found: C, 49.53; H, 5.00; N, 9.10.

Workup

  1. customThe crude product was purified by MPLC

Sources & evidence

ORD record
ord-360bb626fd7645e3a8a264960a6a59be
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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