Water → HCID 118044993, compound

HRID 525744Notes

Reaction equation

C([O:3][C:4](=[O:31])[C:5]1[CH:10]=[C:9]([C:11](=[O:24])[NH:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=2)[CH:8]=[N:7][C:6]=1[N:25]1[CH2:29][CH2:28][C@@H:27]([OH:30])[CH2:26]1)C.[Li+].[OH-].O.O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CCO>[OH:30][C@@H:27]1[CH2:28][CH2:29][N:25]([C:6]2[N:7]=[CH:8][C:9]([C:11](=[O:24])[NH:12][C:13]3[CH:14]=[CH:15][C:16]([O:19][C:20]([F:22])([F:21])[F:23])=[CH:17][CH:18]=3)=[CH:10][C:5]=2[C:4]([OH:31])=[O:3])[CH2:26]1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of (R)-2-(3-hydroxypyrrolidin-1-yl)-5-((4-(trifluoromethoxy)phenyl)carbamoyl)nicotinic acid ethyl ester (Stage 72.4, 3.20 g, 7.28 mmol) and LiOH in EtOH (18 mL)/water (6 mL) was stirred at 50° C. for 8 h. The solution was cooled to RT, acidified with citric acid monohydrate and resulting crystalline title compound was filtered and dried. m.p. 242-245° C., HPLC (Condition 4) tR=4.45 min, UPLC-MS (Condition 8) tR=0.80 min, m/z=412 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.92 (br. s, 2H), 3.10 (d, J=12.12 Hz, 1H), 3.39 (br. s, 1H), 3.50-3.75 (m, 2H), 4.31 (br. s, 1H), 4.80-5.01 (m, 1H), 7.30 (d, J=8.60 Hz, 2H), 7.74-7.88 (m, 2H), 8.39 (d, J=2.35 Hz, 1H), 8.76 (d, J=2.35 Hz, 1H), 10.23 (s, 1H).

Workup

temperatureThe solution was cooled to RT

Sources & evidence

ORD record: ord-4eba0e3af8634b93906e9683368f128c
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340537B2

Reaction notes

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