Ammonia → HCID 66621564, compound

HRID 415160Notes

Reaction equation

HRID 415160 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH:8]2[CH2:12][CH2:11][CH2:10][NH:9]2)[CH:5]=[CH:4][C:3]=1[C:13]1[O:14][C:15]2[C:21]([C:22]([O:24]C)=O)=[CH:20][CH:19]=[CH:18][C:16]=2[N:17]=1.[NH3:26]>CO>[F:1][C:2]1[CH:7]=[C:6]([CH:8]2[CH2:12][CH2:11][CH2:10][NH:9]2)[CH:5]=[CH:4][C:3]=1[C:13]1[O:14][C:15]2[C:21]([C:22]([NH2:26])=[O:24])=[CH:20][CH:19]=[CH:18][C:16]=2[N:17]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 66621285HCID 66621285, compound

Product 1

HCID 66621564HCID 66621564, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 2-(2-fluoro-4-(pyrrolidin-2-yl)phenyl)benzo[d]oxazole-7-carboxylate (200 mg, 1.40 mmol) was added to ammonia in methanol (10 mL) and the mixture was stirred at room temperature for 3 days. The mixture was concentrated, and then purified by prep-HPLC to obtain 2-(2-fluoro-4-(pyrrolidin-2-yl)phenyl)benzo[d]oxazole-7-carboxamide as a white solid (34.6 mg, yield 18%). 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 1.50-1.55 (m, 1H), 1.74-1.79 (m, 2H), 2.18-2.23 (m, 1H), 2.95-3.02 (m, 2H), 4.19-4.23 (m, 1H), 7.42-7.51 (m, 3H), 7.74-7.80 (br s, 1H), 7.80-7.82 (d, J=6.8 Hz, 2H), 7.96-7.98 (dd, J1=7.6 Hz, J2=0.8 Hz, 1H), 8.22 (t, J=8.4 Hz, 1H); LC-MS (ESI) m/z: 326 (M+1)+.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by prep-HPLC

Sources & evidence

ORD record
ord-3aa4435c14224203870c336a6d476a1d
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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