HCID 46735914, compound → HCID 67010388, compound

HRID 1630141Notes

Reaction equation

HRID 1630141 reaction equation
Cl.[CH:2]([N:5]1[CH2:10][CH2:9][N:8]([CH2:11][C:12]([OH:14])=O)[CH2:7][CH2:6]1)([CH3:4])[CH3:3].[NH2:15][C@@H:16]([CH2:34][O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:17]([NH:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)=[CH:22][CH:21]=1)=[O:18]>>[CH2:36]([O:35][CH2:34][C@H:16]([NH:15][C:12](=[O:14])[CH2:11][N:8]1[CH2:7][CH2:6][N:5]([CH:2]([CH3:3])[CH3:4])[CH2:10][CH2:9]1)[C:17]([NH:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)=[CH:22][CH:21]=1)=[O:18])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

3

Reactant 2

HCID 46735914HCID 46735914, compoundHCID 67009137(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide

Product 1

HCID 67010388HCID 67010388, compoundYield 45.1%

Procedure

Proceeding as in Example 1, but substituting 2-(4-isopropylpiperazin-1-yl)acetic acid hydrochloride and (S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide, gave Compound III, (S)-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)-2-(2-(4-isopropylpiperazin-1-yl)acetamido)propanamide (19.8 mg, 45.1%). Major isomer: 1H-NMR (400 MHz, DMSO-D6): σ 10.22 (s, 1H), 7.92 (d, 1H), 7.59 (d, 2H), 7.30 (m, 5H), 7.21 (t, 2H), 7.04-6.98 (m, 4H), 4.70 (m, 1H), 4.52 (s, 2H), 3.77 (m, 1H), 3.71 (m, 1H), 2.96 (d, 2H), 2.61 (m, 1H), 2.50 (t, 8H), 0.95 (d, 6H). MS (EI) for C31H37FN4O4. found 549.7 (MH+).

Sources & evidence

ORD record
ord-e5b0aec400c94522889460c744cd9f22
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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