Ammonia → HCID 57562987, compound

HRID 1726283Notes

Reaction equation

HRID 1726283 reaction equation
[NH3:1].C[O:3][C:4](=O)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]([CH:20]2[CH2:25][CH2:24][N:23]([C@H:26]([CH3:40])[CH2:27][CH2:28][NH:29][C:30]([C:32]3[C:33]([CH3:39])=[N:34][CH:35]=[N:36][C:37]=3[CH3:38])=[O:31])[CH2:22][CH2:21]2)[CH2:14][C:15]2[CH:19]=[CH:18][S:17][CH:16]=2)=[CH:9][CH:8]=1>CO>[C:4]([CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([N:13]([CH2:14][C:15]2[CH:19]=[CH:18][S:17][CH:16]=2)[CH:20]2[CH2:21][CH2:22][N:23]([C@H:26]([CH3:40])[CH2:27][CH2:28][NH:29][C:30]([C:32]3[C:37]([CH3:38])=[N:36][CH:35]=[N:34][C:33]=3[CH3:39])=[O:31])[CH2:24][CH2:25]2)=[CH:11][CH:12]=1)(=[O:3])[NH2:1]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 68972864HCID 68972864, compound

Product 1

HCID 57562987HCID 57562987, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

NH3 (g) was bubbled through a solution of {4-[(1-{(R)-3-[(4,6-dimethyl-pyrimidine-5-carbonyl)-amino]-1-methyl-propyl}-piperidin-4-yl)-thiophen-3-ylmethyl-amino]-phenoxy}-acetic acid methyl ester (see EXAMPLE 297) (54 mg, 0.095 mmol) in MeOH (10 mL) for 10 minutes. The mixture was stirred at room temperature for 1 hour and concentrated under reduced pressure to give COMPOUND 298 as a pale brown solid (52 mg, 100%). 1H NMR (CDCl3) δ 0.89-1.12 (m, 2H), 1.00 (d, 3H, J=6.3 Hz), 1.52-1.63 (m, 1H), 1.74-1.78 (m, 3H), 2.13 (t, 1H, J=11.4 Hz), 2.51 (s, 6H), 2.51-2.57 (m, 1H), 2.72-2.84 (m, 3H), 3.27-3.40 (m, 2H), 3.79 (s, 2H), 3.85-3.89 (m, 1H), 4.40 (s, 2H), 5.59 (br s, 1H), 6.59-6.76 (m, 5H), 6.99 (s, 2H), 8.78 (br s, 1H), 8.86 (s, 1H). ES-MS m/z 551 (M+H).

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fbee600d6e2c4682963fe2e45d7a7851
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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