Ammonia → HCID 71262347, compound

HRID 540235Notes

Reaction equation

HRID 540235 reaction equation
[O:1]=[S:2]1(=[O:37])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][N:5]([C:13]2[CH:22]=[C:21]([NH:23][C:24]3([CH2:28][NH:29]C(=O)C(F)(F)F)[CH2:27][O:26][CH2:25]3)[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([CH3:36])[CH:19]=3)[N:14]=2)[CH2:4][CH2:3]1.N.C[OH:40]>>[NH2:29][CH2:28][C:24]([NH:23][C:21]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([CH3:36])[CH:19]=2)[N:14]=[C:13]([N:5]2[CH2:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[S:2](=[O:37])(=[O:1])[CH2:3][CH2:4]2)[CH:22]=1)([CH2:25][OH:40])[CH2:27][OH:26]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 86691416HCID 86691416, compound

Product 1

HCID 71262347HCID 71262347, compoundYield 25%

Procedure

A mixture of N-[(3-{[2-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylquinolin-4-yl]amino}oxetan-3-yl)methyl]-2,2,2-trifluoroacetamide (269 mg, 0.503 mmol) and a solution of ammonia in methanol (7 M, 10 mL,) was stirred at room temperature overnight. The resulting mixture was concentrated in vacuo and the residue was purified by preparative HPLC to afford 58 mg of the product as a white solid (yield was 25%). MS obsd. (ESI+) [(M+H)+] 457, 1H NMR (400 MHz, CD3OD) δ ppm 8.11-8.09 (t, J=6.4, 1.2 Hz, 1 H), 8.00-7.96 (m, 1 H), 7.86 (s, 1 H), 7.76-7.73 (m, 2 H), 7.64-7.60 (m, 2 H), 6.49 (s, 1 H), 5.33 (s, 2 H), 4.55 (s, 2 H), 3.82 (s, 2 H), 3.77-3.75 (m, 6 H), 2.49 (s, 3 H).

Workup

  1. concentrationThe resulting mixture was concentrated in vacuo
  2. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-636443e1a6924a2799d34c20b79c1e62
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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