Cyanogen Bromide → HCID 86691393, compound

HRID 540160Notes

Reaction equation

HRID 540160 reaction equation
[NH2:1][C@H:2]1[CH2:6][N:5]([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([CH3:17])[CH:15]=3)[N:10]=[C:9]([N:18]3[CH2:24][C:23]4[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=4[S:21](=[O:30])(=[O:29])[CH2:20][CH2:19]3)[CH:8]=2)[CH2:4][C@H:3]1[OH:31].C([O-])(=O)C.[Na+].[N:37]#[C:38]Br>CO>[O:29]=[S:21]1(=[O:30])[C:22]2[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=2[CH2:24][N:18]([C:9]2[CH:8]=[C:7]([N:5]3[CH2:4][C@H:3]4[C@H:2]([N:1]=[C:38]([NH2:37])[O:31]4)[CH2:6]3)[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([CH3:17])[CH:15]=3)[N:10]=2)[CH2:19][CH2:20]1

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 517045Sodium AcetateHCID 71255319HCID 71255319, compound

Product 1

HCID 86691393HCID 86691393, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of cis-4-amino-1-[2-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylquinolin-4-yl]pyrrolidin-3-ol (90 mg 0.20 mmol, prepared in analogy to Example 19-3 in Scheme 7 by using 4-(4-chloro-6-methylquinolin-2-yl)-2,3,4,5-tetrahydro-1,4-benzothiazepine 1,1-dioxide and tert-butyl [cis-4-hydroxypyrrolidin-3-yl]carbamate) and sodium acetate (82 mg, 1.0 mmol) in methanol (10 mL) at 0° C. was added cyanogen bromide (105 mg, 1 mmol). The mixture was stirred overnight gradually from 0° C. to room temperature, and then concentrated in vacuo. The residue was purified by preparative HPLC to afford the pure product as a solid. MS obsd. (ESI+) [(M+H)+] 464, 1H NMR (400 MHz, CD3OD) δ ppm 8.09 (d, J=7.33 Hz, 1 H), 7.98 (d, J=7.58 Hz, 1 H), 7.89 (brs, 1 H), 7.79-7.70 (m, 2 H), 7.66-7.56 (m, 2 H), 6.50 (s, 1 H), 5.89-5.84 (m, 1 H), 5.41 (brs, 2 H), 4.97-5.02 (m, 1 H), 4.63 (brs, 2 H), 4.31 (brs, 1 H), 4.12 (brs, 1 H), 3.77 (brs, 2 H), 3.62-3.42 (b, 2 H), 2.54-2.48 (m, 3 H).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-9b7fc46790284f2ca3ac0549992f5103
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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