Trifluoroacetic acid → HCID 67108619, compound

HRID 1432956Notes

Reaction equation

HRID 1432956 reaction equation
F[C:2](F)(F)[C:3]([OH:5])=O.C(OC([N:15]1[C:23]2[CH:22]=[CH:21][N:20]=[CH:19][C:18]=2[CH:17]=[C:16]1[CH2:24][N:25]1[C:30](=[O:31])[CH2:29][N:28]([S:32]([CH:35]=[CH:36][C:37]2[S:38][C:39]([Cl:42])=[CH:40][CH:41]=2)(=[O:34])=[O:33])C[CH:26]1CO)=O)(C)(C)C>C(Cl)Cl>[Cl:42][C:39]1[S:38][C:37]([CH:36]=[CH:35][S:32]([N:28]2[CH:2]([CH2:3][OH:5])[CH2:26][N:25]([CH2:24][C:16]3[NH:15][C:23]4[CH:22]=[CH:21][N:20]=[CH:19][C:18]=4[CH:17]=3)[C:30](=[O:31])[CH2:29]2)(=[O:34])=[O:33])=[CH:41][CH:40]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54519295HCID 54519295, compound

Product 1

HCID 67108619HCID 67108619, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1.8 mL) is added to a solution of 2-{4-[2-(5-chloro-thiophen-2-yl)-ethenesulfonyl]-2-(±)-hydroxymethyl-6-oxo-piperazin-1-ylmethyl}-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester (0.04 g) in CH2Cl2 (4.2 mL) at RT. The reaction mixture is stirred for 4 h then concentrated in vacuo. The title compound is purified by RP-HPLC eluting in a gradient of 10% CH3CN/H2O (0.1% TFA) to 100% CH3CN and lyophilizing the appropriate product fractions. 1H NMR (DMSO-d6, 300 MHz) δ9.10 (s, 1H), 8.46 (d, 1H), 7.82 (d, 1H), 7.50 (d, 1H) 7.43 (d, 1H), 7.14 (d, 1H), 7.01 (d, 1H), 6.94 (s, 1H), 5.12 (bs, 1H), 4.80 (AB, 2H), 3.98 (d, 2H0, 3.90 (m, 1H), 3.40-3.50 (m, 4H). APCI MS, [M+H]+=467, 469.

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe title compound is purified by RP-HPLC
  3. washeluting in a gradient of 10% CH3CN/H2O (0.1% TFA) to 100% CH3CN

Sources & evidence

ORD record
ord-b514ac8644d34422bbb7d06e525b0f7f
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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