Ethylamine hydrochloride → 1-{[2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}-N-ethyl-1H-pyrrole-3-carboxamide

HRID 1435444Notes

Reaction equation

HRID 1435444 reaction equation
[CH3:1][C:2]([C:6]1[N:10]([CH2:11][CH:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:9]2[CH:18]=[CH:19][C:20]([S:22]([N:25]3[CH:29]=[CH:28][C:27]([C:30]([OH:32])=O)=[CH:26]3)(=[O:24])=[O:23])=[CH:21][C:8]=2[N:7]=1)([CH3:5])CC.CN(C(O[N:41]1N=N[C:43]2C=CC=N[C:42]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[CH2:58](N)C>CN(C=O)C>[C:2]([C:6]1[N:10]([CH2:11][CH:12]2[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)[C:9]2[CH:18]=[CH:19][C:20]([S:22]([N:25]3[CH:29]=[CH:28][C:27]([C:30]([NH:41][CH2:42][CH3:43])=[O:32])=[CH:26]3)(=[O:23])=[O:24])=[CH:21][C:8]=2[N:7]=1)([CH3:1])([CH3:58])[CH3:5]

Participants

5

Reactant 3

HCID 11198Ethylamine hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 579373541-(2-tert-pentyl-1-((tetrahydro-2H-pyran-4-yl)methyl)-1H-benzo[d]imidazol-5-ylsulfonyl)-1H-pyrrole-3-carboxylic acid

Product 1

HCID 236601121-{[2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}-N-ethyl-1H-pyrrole-3-carboxamideYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following the same procedure in Example 24, Step A, using DIPLA (105 uL, 78 mg, 0.60 mmol), 1-{[2-(1,1-dimethylpropyl)-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}-1H-pyrrole-3-carboxylic acid (0.85 mmol) (see following Steps B and C for preparation) in DMF (15 mL), HATU (582 mg, 10.53 mmol) and ethylamine hydrochloride (154 mg, 1.87 mmol). The crude product was purified by MPLC on silica gel using EtOAc to give 0.32 g (81%) of a white solid as the title compounds 1H NMR (400 MHz, CHLOROFORM-D) δ 1.19 (t, J=7.23 Hz, 3 H), 1.45-1.54 (m, 4 H), 1.56 (s, 9 H), 2.15-2.33 (m, 1 H), 3.26-3.35 (m, 2 H), 3.36-3.44 (m, 2 H), 3.93-4.03 (m, 2 H), 4.22 (d, J=7.42 Hz, 2H), 5.79 (t, J=5.66 Hz, 1 H), 6.47 (dd, J=3.22, 1.66 Hz, 1 H), 7.17 (dd, J=3.32, 2.15 Hz, 1 H), 7.41 (d, J=8.59 Hz, 1 H) 7.62 (dd, J=2.34, 1.76 Hz, 1 H), 7.76 (dd, J=8.69, 1.86 Hz, 1 H), 8.32 (d, J=1.76 Hz, 1 H); MS (ESI) (M+H)+=473.3.

Workup

  1. customThe crude product was purified by MPLC on silica gel

Sources & evidence

ORD record
ord-b9112f18dd89446c8ff48c5181efb65d
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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