Morpholine → HCID 57563193, compound

HRID 1726217Notes

Reaction equation

HRID 1726217 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:38]=[CH:39][CH:40]=1)[CH2:6][N:7]([CH:17]1[CH2:22][CH2:21][N:20]([CH:23]([CH3:37])[CH2:24][CH2:25][NH:26][C:27]([C:29]2[C:30]([CH3:36])=[N:31][CH:32]=[N:33][C:34]=2[CH3:35])=[O:28])[CH2:19][CH2:18]1)[C:8]1[CH:16]=[CH:15][C:11]([C:12](O)=[O:13])=[CH:10][CH:9]=1)#[N:2].[NH:41]1[CH2:46][CH2:45][O:44][CH2:43][CH2:42]1>>[C:1]([C:3]1[CH:4]=[C:5]([CH:38]=[CH:39][CH:40]=1)[CH2:6][N:7]([C:8]1[CH:16]=[CH:15][C:11]([C:12]([N:41]2[CH2:46][CH2:45][O:44][CH2:43][CH2:42]2)=[O:13])=[CH:10][CH:9]=1)[CH:17]1[CH2:22][CH2:21][N:20]([CH:23]([CH3:37])[CH2:24][CH2:25][NH:26][C:27]([C:29]2[C:34]([CH3:35])=[N:33][CH:32]=[N:31][C:30]=2[CH3:36])=[O:28])[CH2:19][CH2:18]1)#[N:2]

Participants

3

Reactant 2

HCID 8083MorpholineHCID 68971776HCID 68971776, compound

Product 1

HCID 57563193HCID 57563193, compoundYield 87.5%

Procedure

Using general procedure E, 4-[(3-cyano-benzyl)-(1-{3-[(4,6-dimethyl-pyrimidine-5-carbonyl)-amino]-1-methyl-propyl}-piperidin-4-yl)-amino]-benzoic acid (see EXAMPLE 129) (50 mg, 0.09 mmol) and morpholine (29 μL, 0.33 mmol) afforded COMPOUND 167 as a white solid (48 mg, 87%). 1H NMR (CDCl3) δ 0.84-1.18 (m, 2H), 1.03 (d, 3H, J=6.6 Hz), 1.50-1.60 (m, 1H), 1.70-1.84 (m, 3H), 2.14-2.26 (m, 1H), 2.51 (s, 6H), 2.53-2.65 (m, 1H), 2.71-2.92 (m, 3H), 3.27-3.39 (m, 1H), 3.57-3.92 (m, 10H), 3.96 (s, 2H), 6.52 (d, 2H, J=8.4 Hz), 7.25-7.30 (m, 2H), 7.43-7.59 (m, 4H), 8.54 (br s, 1H), 8.90 (s, 1H). 13C NMR (CDCl3) δ 13.84, 22.36, 29.54, 30.83, 31.12, 40.49, 43.87, 48.45, 52.39, 56.04, 60.76, 67.36, 77.61, 112.53, 113.14, 123.98, 129.89, 130.08, 131.17, 141.51, 149.88, 157.99, 163.53, 166.57, 171.00. ES-MS m/z 610 (M+H). Anal. Calcd. for C35H43N7O3.0.2CH2Cl2.0.1H2O: C, 67.26; H, 6.99; N, 15.60. Found. C, 67.44; H, 7.12; N, 15.30.

Sources & evidence

ORD record
ord-52cc7bfb3d3e400cbc839faa54bc9bb0
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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