Sodium Hydroxide → (5-tert-Butyl)-3-(5,6,7,8-tetrahydrobenzo[1,2-b]pyrimidino[5,6-d]selenophen-4-ylamino)thiophene-2-carboxamide

HRID 1529822Notes

Reaction equation

HRID 1529822 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.[C:15]([C:19]1[S:23][C:22]([C:24]([NH2:26])=[O:25])=[C:21]([NH2:27])[CH:20]=1)([CH3:18])([CH3:17])[CH3:16].[OH-].[Na+]>CN(C=O)C>[C:15]([C:19]1[S:23][C:22]([C:24]([NH2:26])=[O:25])=[C:21]([NH:27][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)[CH:20]=1)([CH3:18])([CH3:16])[CH3:17]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 27352933-Amino-5-(Tert-Butyl)Thiophene-2-CarboxamideHCID 867005014-Chloro-5,6,7,8-tetrahydrobenzo[1,2-b]pyrimidino[5,4-d]selenophene

Product 1

HCID 57377311(5-tert-Butyl)-3-(5,6,7,8-tetrahydrobenzo[1,2-b]pyrimidino[5,6-d]selenophen-4-ylamino)thiophene-2-carboxamide

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 (700 mg, 2.57 mmol, from step b of example 1) in DMF (10 mL) was added sequentially 5-tert-butyl-3-aminothiophene-2-carboxamide (700 mg, 3.6 mmol) and powdered NaOH (310 mg, 7.7 mmol) at rt. Work-up of the mixture as described in example 2, gave the product as a yellow color solid, mp 240-244° C. 1H NMR (400 MHz, DMSO-d6): δ 11.38 (1H, s, exchangeable with D2O), 8.45 (1H, s), 8.27 (1H, s), 7.53 (2H, s, exchangeable with D2O), 3.15 (2H, br s), 2.90 (2H, br s), 1.84-1.85 (4H, m), 1.39 (9H, s); 13C NMR (100 MHz, DMSO-d6): δ 170.9, 166.1, 158.0, 153.1, 151.4, 143.4, 138.2, 128.2, 119.5, 119.2, 109.2, 34.5, 31.7, 27.7, 27.4, 22.4, 22.1; LC-MS (positive ion mode): m/z 433, 435 (M+H)+.

Workup

  1. customgave the product as a yellow color solid, mp 240-244° C

Sources & evidence

ORD record
ord-6796d6294bb94a26a3cac99e5f6b3243
Source dataset
uspto-grants-2015_07
Patent number
US09090633B2

Reaction notes

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