HCID 59140918, compound → HCID 57849778, compound

HRID 737182Notes

Reaction equation

HRID 737182 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([NH:14][C:15](=[O:45])[C:16]2[CH:21]=[CH:20][C:19]([C:22]3[N:23]=[C:24]([NH:27][C:28]([CH:30]4[CH2:34][CH2:33][CH2:32][N:31]4[C:35]([O:37][CH2:38][C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)=[O:36])=[O:29])[S:25][CH:26]=3)=[CH:18][CH:17]=2)[CH2:9]1)=O)(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[CH2:38]([O:37][C:35]([N:31]1[CH2:32][CH2:33][CH2:34][CH:30]1[C:28](=[O:29])[NH:27][C:24]1[S:25][CH:26]=[C:22]([C:19]2[CH:20]=[CH:21][C:16]([C:15](=[O:45])[NH:14][CH:10]3[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]3)=[CH:17][CH:18]=2)[N:23]=1)=[O:36])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

3

Reactant 1

HCID 59140918HCID 59140918, compound2×

Product 1

HCID 57849778HCID 57849778, compound

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

3-(4-{2-[(1-Benzyloxycarbonyl-pyrrolidine-2-carbonyl)-amino]-thiazol-4-yl}-benzoylamino)-piperidine-1-carboxylic acid tert butyl ester (Compound 5336, Example 336, 100 mg, 0.16 mmol) was dissolved in 4 mL of 1:1 solution of CH2Cl2/TFA and stirred for 1.5 at room temperature. Reaction mixture was evaporated under reduced pressure to give pure desired product. MS: 534.2(M+H+); H1 NMR (MeOH-d4): δ(ppm) (HCl salt)12.47 (s, 1H), 9.52 (s, 1H), 8.64 (s, 1H), 7.95 (m, 5H), 7.50 (br s, 2H), 7.08 (d, 2H), 5.03 (m, 2H), 4.49 (m, 1H), 4.12 (m, 1H), 3.68-2.96 (m, 6H), 2.28 (m, 1H), 1.90 (m, 8H).

Workup

  1. customReaction mixture
  2. customwas evaporated under reduced pressure

Sources & evidence

ORD record
ord-6fc0898648884eae93243ba157cad27d
Source dataset
uspto-grants-2009_09
Patent number
US07595398B2

Reaction notes

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