methyl L-prolinate hydrochloride → (S)-1-{3-[3-(6-Fluoro-benzothiazol-2-ylamino)-phenyl]-isoxazole-5-carbonyl}-pyrrolidine-2-carboxylic acid methyl ester

HRID 75770

Reaction equation

HRID 75770 reaction equation
[F:1][C:2]1[CH:25]=[CH:24][C:5]2[N:6]=[C:7]([NH:9][C:10]3[CH:11]=[C:12]([C:16]4[CH:20]=[C:19]([C:21](O)=[O:22])[O:18][N:17]=4)[CH:13]=[CH:14][CH:15]=3)[S:8][C:4]=2[CH:3]=1.Cl.[CH3:27][O:28][C:29]([C@@H:31]1[CH2:35][CH2:34][CH2:33][NH:32]1)=[O:30]>>[CH3:27][O:28][C:29]([C@@H:31]1[CH2:35][CH2:34][CH2:33][N:32]1[C:21]([C:19]1[O:18][N:17]=[C:16]([C:12]2[CH:13]=[CH:14][CH:15]=[C:10]([NH:9][C:7]3[S:8][C:4]4[CH:3]=[C:2]([F:1])[CH:25]=[CH:24][C:5]=4[N:6]=3)[CH:11]=2)[CH:20]=1)=[O:22])=[O:30]

Participants

3

Reactant 2

HCID 2733200methyl L-prolinate hydrochlorideHCID 866564873-[3-(6-Fluoro-benzothiazol-2-ylamino)-phenyl]-isoxazole-5-carboxylic acid

Product 1

HCID 46180895(S)-1-{3-[3-(6-Fluoro-benzothiazol-2-ylamino)-phenyl]-isoxazole-5-carbonyl}-pyrrolidine-2-carboxylic acid methyl esterYield 41%

Procedure

The title compound was prepared according to the procedure as set forth in Example 5, except that 3-[3-(6-fluoro-benzothiazol-2-ylamino)-phenyl]-isoxazole-5-carboxylic acid was used instead of the compound of Example 2 and (S)-pyrrolidine-2-carboxylic acid methyl ester hydrochloride was used in place of (S)-Val-OMe.HCl to yield 41% of the title compound. Mass (ES+): 467 (M++1), 489 (M++Na); IR (KBr): 3295, 3110, 2951, 1742, 1626, 1613, 1568 (br), 1454, 1411; 1H NMR (DMSO-d6) δ: 1.70-2.39 (4×m, 4H), 3.65 (s, 3H), 3.64, 3.92 (2×m, 2H), 4.55, 5.10 (2×m, 1H), 7.17 (m, 1H), 7.52-7.64 (m, 3H), 7.65 (s, 1H), 7.75 (dd, 1H), 7.95 (m, 1H), 8.32 (m, 1H), 10.68 (s, 1H).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-4927a20103e54bb1a69c2a5ecf1660db
Source dataset
uspto-grants-2014_09
Patent number
US08835428B2

Linked notes

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