2'-[[(Methylamino)carbonyl]amino]methyl-1,1'-biphenyl-4-methanol → 3-[[2,2-Dimethyl-1,3-dioxolan-4(S)-yl]methyl]amino-3-methyl-N-[2,3,4,5-tetrahydro-1-[[2'-[[[(methylamino)carbonyl]amino]methyl][1,1'-biphenyl]-4-yl]methyl]-2-oxo-1H-benzazepin-3(R)-yl]butanamide

HRID 1740240Notes

Reaction equation

HRID 1740240 reaction equation
[CH3:1][C:2]1([CH3:28])[O:6][C@@H:5]([CH2:7][NH:8][C:9]([CH3:27])([CH3:26])[CH2:10][C:11]([NH:13][C@@H:14]2[CH2:20][CH2:19][C:18]3[CH:21]=[CH:22][CH:23]=[CH:24][C:17]=3[NH:16][C:15]2=[O:25])=[O:12])[CH2:4][O:3]1.[CH3:29][NH:30][C:31]([NH:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[C:41]1[CH:46]=[CH:45][C:44]([CH2:47]O)=[CH:43][CH:42]=1)=[O:32]>>[CH3:1][C:2]1([CH3:28])[O:6][C@@H:5]([CH2:7][NH:8][C:9]([CH3:27])([CH3:26])[CH2:10][C:11]([NH:13][C@@H:14]2[CH2:20][CH2:19][C:18]3[CH:21]=[CH:22][CH:23]=[CH:24][C:17]=3[N:16]([CH2:47][C:44]3[CH:43]=[CH:42][C:41]([C:36]4[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=4[CH2:34][NH:33][C:31]([NH:30][CH3:29])=[O:32])=[CH:46][CH:45]=3)[C:15]2=[O:25])=[O:12])[CH2:4][O:3]1

Participants

3

Reactant 2

HCID 111732732'-[[(Methylamino)carbonyl]amino]methyl-1,1'-biphenyl-4-methanolHCID 228774543-[[2,2-Dimethyl-1,3-dioxolan-4(S)-yl]methyl]amino-3-methyl-N-[2,3,4,5-tetrahydro-2-oxo-1H-benzazepin-3(R)-yl]butanamide

Product 1

HCID 228774533-[[2,2-Dimethyl-1,3-dioxolan-4(S)-yl]methyl]amino-3-methyl-N-[2,3,4,5-tetrahydro-1-[[2'-[[[(methylamino)carbonyl]amino]methyl][1,1'-biphenyl]-4-yl]methyl]-2-oxo-1H-benzazepin-3(R)-yl]butanamide

Procedure

Prepared from 3-[[2,2-dimethyl-1,3-dioxolan-4(S)-yl]-methyl]amino-3-methyl-N-[2,3,4,5-tetrahydro-2-oxo-1H-benzazepin-3(R)-yl]butanamide (Step B) and 2'-[[(methylamino)carbonyl]amino]methyl-1,1'-biphenyl-4-methanol, methanesulfonate ester (Example 48, Step I) according to the procedure described in Example 35, Step H.1H NMR (200 MHz, CD3OD): δ 1.14 (s, 6H), 1.28 (s, 3H), 1.34 (s, 3H), 2.07 (m, 1H), 2.20-2.42 (m, 3H), 2.48-2.76 (m, 4H), 2.64 (s, 3H), 3.64 dd; 8, 6 Hz; 1H), 4.05 (dd; 8, 6 Hz; 1H), 4.14 (s, 2H), 4.20 (m, 1H), 4.40 (dd; 12, 8 Hz; 1H), 4.94 (d, 15 Hz, 1H), 5.27 (d, 15 Hz, 1H), 7.10-7.40 (m, 12H). FAB-MS: calculated for C37H46N5O5 641; found 642 (M+H, 80%).

Sources & evidence

ORD record
ord-86235e0be0a343e9afd77b14a51fcb8c
Source dataset
uspto-grants-1999_10
Patent number
US05968924

Reaction notes

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