HCID 17221248, compound → HCID 67010465, compound

HRID 1630134Notes

Reaction equation

HRID 1630134 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[N:4][C:3]=1[N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]([OH:17])=O)[CH2:10][CH2:9]1.[NH2:18][C@@H:19]([CH2:37][O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:20]([NH:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)=[CH:25][CH:24]=1)=[O:21]>>[CH2:39]([O:38][CH2:37][C@H:19]([NH:18][C:15](=[O:17])[CH2:14][N:11]1[CH2:10][CH2:9][N:8]([C:3]2[N:2]=[CH:7][CH:6]=[CH:5][N:4]=2)[CH2:13][CH2:12]1)[C:20]([NH:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)=[CH:25][CH:24]=1)=[O:21])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

3

Reactant 2

HCID 17221248HCID 17221248, compoundHCID 67009137(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide

Product 1

HCID 67010465HCID 67010465, compoundYield 36.6%

Procedure

Proceeding as in Example 1, but substituting 2-(4-(pyrimidin-2-yl)piperazin-1-yl)acetic acid hydrochloride and (S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide, gave Compound 41, (S)-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)-2-(2-(4-(pyrimidin-2-yl)piperazin-1-yl)acetamido)propanamide (17.1 mg, 36.6%). 1H-NMR (400 MHz, DMSO-D6): σ 10.22 (s, 1H), 8.36 (d, 2H), 8.06 (d, 1H), 7.60 (d, 2H), 7.23 (m, 7H), 7.02 (m, 4H), 6.63 (t, 1H), 4.71 (m, 1H), 4.53 (s, 2H), 3.73 (m, 7H), 3.06 (s, 2H), 2.54 (m, 5H). MS (EI) for C32H33FN6O4: 585.6 (MH+).

Sources & evidence

ORD record
ord-3867ffd334704656a72d5112e804bf0d
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

Loading…