Diisopropylethylamine → 4-({2-tert-butyl-1-[(4,4-difluorocyclohexyl)methyl]-1H-benzimidazol-5-yl}sulfonyl)morpholine-2-carboxylic acid

HRID 1435520Notes

Reaction equation

HRID 1435520 reaction equation
[C:1]([C:5]1[N:9]([CH2:10][CH:11]2[CH2:16][CH2:15][C:14]([F:18])([F:17])[CH2:13][CH2:12]2)[C:8]2[CH:19]=[CH:20][C:21]([S:23](Cl)(=[O:25])=[O:24])=[CH:22][C:7]=2[N:6]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)C(C)C)(C)C.Cl.[NH:37]1[CH2:42][CH2:41][O:40][CH:39]([C:43]([OH:45])=[O:44])[CH2:38]1>C(Cl)Cl>[C:1]([C:5]1[N:9]([CH2:10][CH:11]2[CH2:16][CH2:15][C:14]([F:18])([F:17])[CH2:13][CH2:12]2)[C:8]2[CH:19]=[CH:20][C:21]([S:23]([N:37]3[CH2:42][CH2:41][O:40][CH:39]([C:43]([OH:45])=[O:44])[CH2:38]3)(=[O:25])=[O:24])=[CH:22][C:7]=2[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 42614320Morpholine-2-carboxylic acid hydrochlorideHCID 579372942-tert-Butyl-1-[(4,4-difluorocyclohexyl)methyl]-1H-benzimidazole-5-sulfonyl chloride

Product 1

HCID 579373664-({2-tert-butyl-1-[(4,4-difluorocyclohexyl)methyl]-1H-benzimidazol-5-yl}sulfonyl)morpholine-2-carboxylic acidYield 75.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the same procedure in Example 1, Step A, using 2-tert-butyl-1-[(4,4-difluorocyclohexyl)methyl]-1H-benzimidazole-5-sulfonyl chloride (1.6 g, 4 mmol), N,N-diisopropylethylamine (3.5 mL, 20 mmol) and morpholine-2-carboxylic acid hydrochloride (1.0 g, 6 mmol) in methylene chloride (10 mL). Obtained 1.5 g of crude product which was carried over to step A. 1H NMR (400 MHz, METHANOL-D4) δ 1.53 (d, J=13.67 Hz, 2 H), 1.59 (s, 12 H), 1.63-1.78 (m, 6 H), 1.98-2.12 (m, 3 H), 3.22 (q, J=7.36 Hz, 1 H), 3.72 (m, 1 H), 4.42 (d, J=7.42 Hz, 2 H), 7.69 (d, J=8.40 Hz, 1 H), 7.81 (d, J=8.40 Hz, 1 H), 8.05 (s, 1 H).

Sources & evidence

ORD record
ord-c4d7fc08b94340c4a0587251b93a8ab7
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

Loading…