Water → 2-(6-Amino-7-bromo-2,3-dihydro-4h-1,4-benzoxazin-4-yl)-6,6-dimethyl-6,7-dihydro[1,3]thiazolo[5,4-c]pyridin-4(5h)-one

HRID 885967Notes

Reaction equation

HRID 885967 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][CH2:8][N:7]([C:11]3[S:12][C:13]4[C:14](=[O:22])[NH:15][C:16]([CH3:21])([CH3:20])[CH2:17][C:18]=4[N:19]=3)[C:6]=2[CH:23]=1.C1C(=O)N([Br:31])C(=O)C1.O>C(Cl)Cl>[NH2:1][C:2]1[C:3]([Br:31])=[CH:4][C:5]2[O:10][CH2:9][CH2:8][N:7]([C:11]3[S:12][C:13]4[C:14](=[O:22])[NH:15][C:16]([CH3:21])([CH3:20])[CH2:17][C:18]=4[N:19]=3)[C:6]=2[CH:23]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 58441690HCID 58441690, compound

Product 1

HCID 671854432-(6-Amino-7-bromo-2,3-dihydro-4h-1,4-benzoxazin-4-yl)-6,6-dimethyl-6,7-dihydro[1,3]thiazolo[5,4-c]pyridin-4(5h)-oneYield 12.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of Example 42 (0.04 g, 0.12 mmol) in DCM (1 mL) was added NBS (0.02 g, 0.12 mmol) and the reaction mixture stirred for 1 h at r.t. Water (2 mL) was added, the layers were separated and the organic fraction was concentrated in vacuo. Purification by preparative HPLC (Method 6) gave the title compound (0.006 g, 12%) as a white solid. δH (CDCl3) 7.56 (1H, s), 7.05 (1H, s), 5.30 (1H, s), 4.29-4.23 (2H, m), 4.11-4.05 (2H, m), 2.88 (2H, s), 1.40 (6H, s). LCMS (ES+) 409.2 and 411.2 (1:1 ratio) (M+H)+, RT 3.06 minutes (Method 1).

Workup

  1. customthe layers were separated
  2. concentrationthe organic fraction was concentrated in vacuo
  3. customPurification by preparative HPLC (Method 6)

Sources & evidence

ORD record
ord-0d8534e12da344aaa7ade82b41028653
Source dataset
uspto-grants-2012_08
Patent number
US08242116B2

Reaction notes

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