HCID 86654946, compound → HCID 58327182, compound

HRID 391977Notes

Reaction equation

HRID 391977 reaction equation
C[O:2][C:3](=[O:66])[C@@H:4]([NH:20][C:21]([C@@H:23]1[CH2:32][C:31]2[CH:30]=[C:29]3[O:33][CH2:34][C@H:35]([C:37]4[CH:42]=[CH:41][C:40]([O:43][CH2:44][C:45]5[CH:50]=[CH:49][C:48]([Cl:51])=[C:47]([Cl:52])[CH:46]=5)=[CH:39][CH:38]=4)[O:36][C:28]3=[CH:27][C:26]=2[CH2:25][N:24]1[S:53]([C:56]1[S:60][C:59]([NH:61]C(=O)C)=[N:58][C:57]=1[CH3:65])(=[O:55])=[O:54])=[O:22])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([CH3:18])[C:13]=2[CH3:19])=[CH:8][CH:7]=1.COC(=O)[C@@H](NC([C@@H]1CC2C=C3OC[C@H](C4C=CC(OCC5C=CC(Cl)=C(Cl)C=5)=CC=4)OC3=CC=2CN1S(C1SC(N)=NC=1C)(=O)=O)=O)CC1C=CC(C2C=CN=C(C)C=2C)=CC=1>>[NH2:61][C:59]1[S:60][C:56]([S:53]([N:24]2[C@H:23]([C:21]([NH:20][C@@H:4]([CH2:5][C:6]3[CH:7]=[CH:8][C:9]([C:12]4[CH:17]=[CH:16][N:15]=[C:14]([CH3:18])[C:13]=4[CH3:19])=[CH:10][CH:11]=3)[C:3]([OH:66])=[O:2])=[O:22])[CH2:32][C:31]3[CH:30]=[C:29]4[O:33][CH2:34][C@H:35]([C:37]5[CH:42]=[CH:41][C:40]([O:43][CH2:44][C:45]6[CH:50]=[CH:49][C:48]([Cl:51])=[C:47]([Cl:52])[CH:46]=6)=[CH:39][CH:38]=5)[O:36][C:28]4=[CH:27][C:26]=3[CH2:25]2)(=[O:54])=[O:55])=[C:57]([CH3:65])[N:58]=1

Participants

3

Reactant 2

HCID 86654946HCID 86654946, compoundHCID 86654947HCID 86654947, compound

Product 1

HCID 58327182HCID 58327182, compound

Procedure

(S)-2-({(3S,8S)-7-(2-acetylamino-4-methyl-thiazole-5-sulfonyl)-3-[4-(3,4-dichloro-benzyloxy)-phenyl]-2,3,6,7,8,9-hexahydro-[1,4]dioxino[2,3-g]isoquinoline-8-carbonyl}-amino)-3-[4-(2,3-dimethyl-pyridin-4-yl)-phenyl]-propionic acid methyl ester was converted to (S)-2-({(3S,8S)-7-(2-amino-4-methyl-thiazole-5-sulfonyl)-3-[4-(3,4-dichloro-benzyloxy)-phenyl]-2,3,6,7,8,9-hexahydro-[1,4]dioxino[2,3-g]isoquinoline-8-carbonyl}-amino)-3-[4-(2,3-dimethyl-pyridin-4-yl)-phenyl]-propionic acid methyl ester according to General Procedure N. This ester (20 mg) was hydrolyzed according to General Procedure B to give the title compound (17 mg). LCMS (m/z): 915.

Sources & evidence

ORD record
ord-3817f9a1e17944f18fbe715aaa5e2184
Source dataset
uspto-grants-2013_02
Patent number
US08383644B2

Reaction notes

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