Sodium Hydroxide → HCID 57377416, compound

HRID 1529826Notes

Reaction equation

HRID 1529826 reaction equation
Cl[C:2]1[C:7]2[C:8]3[CH2:14][CH2:13][CH2:12][CH2:11][C:9]=3[Se:10][C:6]=2[N:5]=[CH:4][N:3]=1.[CH3:15][S:16][C:17]1[S:18][C:19]([N+:23]([O-:25])=[O:24])=[C:20]([NH2:22])[N:21]=1.[OH-].[Na+]>CN(C=O)C>[CH3:15][S:16][C:17]1[S:18][C:19]([N+:23]([O-:25])=[O:24])=[C:20]([NH:22][C:2]2[C:7]3[C:8]4[CH2:14][CH2:13][CH2:12][CH2:11][C:9]=4[Se:10][C:6]=3[N:5]=[CH:4][N:3]=2)[N:21]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 27612814-Amino-2-methylthio-5-nitrothiazoleHCID 867005014-Chloro-5,6,7,8-tetrahydrobenzo[1,2-b]pyrimidino[5,4-d]selenophene

Product 1

HCID 57377416HCID 57377416, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-chloro-5,6,7,8-tetrahydrobenzo[1,2-b]pyrimidino[5,4-d]selenophene (420 mg, 1.57 mmol) in DMF (8 mL) was added sequentially 2-(methylthio)-5-nitrothiazol-4-amine (300 mg, 1.57 mmol) and powdered NaOH (180 mg, 4.71 mmol) at rt. Work-up as described in example 2, gave the product as a yellow color solid, mp 204-206° C. 1H NMR (400 MHz, CDCl3): δ 10.52 (1H, s, exchangeable with D2O, —NH), 8.73 (1H, s, H-2), 3.11 (2H, t, J=5.2 Hz, H-8), 2.98 (2H, t, J=5.0 Hz, H-5), 2.75 (3H, s, —SCH3), 1.92-1.98 (4H, m, H-6,7); 13C NMR (100 MHz, CDCl3): δ 176.9, 173.7, 152.2, 151.6, 151.1, 150.9, 142.7, 127.4, 124.1, 28.4, 28.0, 22.8, 22.5, 16.1; LC-MS (positive ion mode): m/z 426, 428 (M+H)+.

Workup

  1. customgave the product as a yellow color solid, mp 204-206° C

Sources & evidence

ORD record
ord-0793c024b38e437c8df6b96e523975e5
Source dataset
uspto-grants-2015_07
Patent number
US09090633B2

Reaction notes

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