Hydrochloric Acid → [4-(4-Chloro-3-dibutylcarbamoyl-5-methyl-pyrazol-1-yl)-3-((S)-3-hydroxymethyl-3,4-dihydro-1H-isoquinoline-2-carbonyl)-phenoxy]-acetic acid

HRID 2274607Notes

Reaction equation

HRID 2274607 reaction equation
C([O:3][C:4](=[O:45])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:17]([CH3:18])=[C:16]([Cl:19])[C:15]([C:20](=[O:30])[N:21]([CH2:26][CH2:27][CH2:28][CH3:29])[CH2:22][CH2:23][CH2:24][CH3:25])=[N:14]2)=[C:9]([C:31]([N:33]2[C@H:42]([CH2:43][OH:44])[CH2:41][C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH2:34]2)=[O:32])[CH:8]=1)C.Cl>[OH-].[Na+].CO>[Cl:19][C:16]1[C:15]([C:20](=[O:30])[N:21]([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:26][CH2:27][CH2:28][CH3:29])=[N:14][N:13]([C:10]2[CH:11]=[CH:12][C:7]([O:6][CH2:5][C:4]([OH:45])=[O:3])=[CH:8][C:9]=2[C:31]([N:33]2[C@H:42]([CH2:43][OH:44])[CH2:41][C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH2:34]2)=[O:32])[C:17]=1[CH3:18]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 71617712[4-(4-Chloro-3-dibutylcarbamoyl-5-methyl-pyrazol-1-yl)-3-((S)-3-hydroxymethyl-3,4-dihydro-1H-isoquinoline-2-carbonyl)-phenoxy]-acetic acid ethyl ester

Product 1

HCID 71617713[4-(4-Chloro-3-dibutylcarbamoyl-5-methyl-pyrazol-1-yl)-3-((S)-3-hydroxymethyl-3,4-dihydro-1H-isoquinoline-2-carbonyl)-phenoxy]-acetic acidYield 20%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of [4-(4-chloro-3-dibutylcarbamoyl-5-methyl-pyrazol-1-yl)-3-((S)-3-hydroxymethyl-3,4-dihydro-1H-isoquinoline-2-carbonyl)-phenoxy]-acetic acid ethyl ester (10 mg, 0.016 mmol) in sodium hydroxide (2N, 0.039 mL) and methanol (0.1 mL) was stirred at ambient temperature for 12 hours. Added aqueous HCl solution until pH is about 5. The crude material was purified by HPLC to afford the title compound (1.9 mg, 20% yield). MS (ESI) [m/e, (M+H)+]=611.5. 1H NMR (400 MHz, chloroform-d) δ ppm 6.78-7.37 (m, 7H), 4.08-5.51 (m, 5H), 2.33-3.75 (m, 8H), 2.13-2.33 (m, 3H), 0.60-1.72 (m, 14H).

Workup

  1. customThe crude material was purified by HPLC

Sources & evidence

ORD record
ord-4778b2e30aa04272bcb4a41bf9ff4c70
Source dataset
uspto-grants-2015_09
Patent number
US09126979B2

Reaction notes

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