Benzenemethanamine, N-butyl- → HCID 71062227, compound

HRID 528915Notes

Reaction equation

HRID 528915 reaction equation
[Cl:1][C:2]1[C:3]([C:42]([OH:44])=O)=[N:4][N:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:29])[NH:15][S:16]([C:19]3[CH:28]=[CH:27]C4C(=CC=CC=4)[CH:20]=3)(=[O:18])=[O:17])=[CH:10][C:9]=2[C:30]([N:32]2[CH2:41][CH2:40][C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH2:33]2)=[O:31])[C:6]=1[CH3:7].[CH2:45]([NH:52][CH2:53][CH2:54][CH2:55][CH3:56])[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1>>[CH2:45]([N:52]([CH2:53][CH2:54][CH2:55][CH3:56])[C:42]([C:3]1[C:2]([Cl:1])=[C:6]([CH3:7])[N:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:29])[NH:15][S:16]([C:19]3[CH:20]=[CH:11][C:10]4[C:27](=[CH:12][CH:13]=[CH:8][CH:9]=4)[CH:28]=3)(=[O:17])=[O:18])=[CH:10][C:9]=2[C:30]([N:32]2[CH2:33][CH2:34][C:35]3[C:40](=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH2:41]2)=[O:31])[N:4]=1)=[O:44])[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1

Participants

3

Reactant 2

HCID 75467Benzenemethanamine, N-butyl-HCID 71062224HCID 71062224, compound2×

Product 1

HCID 71062227HCID 71062227, compoundYield 135.6%

Procedure

Following a procedure analogous to that for the synthesis of Example 125, 4-chloro-5-methyl-1-(4-(naphthalen-2-ylsulfonylcarbamoyl)-2-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)phenyl)-1H-pyrazole-3-carboxylic acid (Intermediate 122F, 25 mg, 0.040 mmol) and N-benzylbutan-1-amine (Aldrich, 11 μL, 0.064 mmol) were converted to the title compound (21 mg, 68%). 1H NMR (1:1 CD3OD:CDCl3) δ 8.62 (br s, 1H), 8.15 (d, J=7.9 Hz, 1H), 8.07-7.82 (m, 5H), 7.64-7.50 (m, 1H), 7.46-7.36 (m, 1.5H), 7.28-6.93 (m, 9H), 6.86 (d, J=7.3 Hz, 0.5H), 4.62 (d, J=5.9 Hz, 1H), 4.47-4.11 (m, 2.5H), 3.77-3.36 (m, 2.5H), 3.21-2.94 (m, 1.5H), 2.81-2.65 (m, 2.5H), 2.35-2.14 (m, 3H), 1.74-1.13 (m, 3H), 1.08-0.77 (m, 3H), 0.72-0.58 (m, 1H); MS(ESI+) m/z 774.1 (M+H)+.

Sources & evidence

ORD record
ord-65b45e3c7642485d9863e006119770b1
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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