tert-Butyl carbazate → HCID 68857890, compound

HRID 1986333Notes

Reaction equation

Cl.Cl.Cl.[Cl:4][C:5]1[C:6]([C:22]2[S:26][C:25]3[CH:27]=[CH:28][CH:29]=[C:30]([C:31](O)=[O:32])[C:24]=3[CH:23]=2)=[N:7][C:8]([NH:11][CH2:12][CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]2)=[N:9][CH:10]=1.[C:34]([O:38][C:39](=[O:42])[NH:40][NH2:41])([CH3:37])([CH3:36])[CH3:35].C(N(C(C)C)CC)(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[Cl-].[Li+]>CN(C=O)C>[C:34]([O:38][C:39]([NH:40][NH:41][C:31]([C:30]1[C:24]2[CH:23]=[C:22]([C:6]3[C:5]([Cl:4])=[CH:10][N:9]=[C:8]([NH:11][CH2:12][CH2:13][CH2:14][N:15]4[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]4)[N:7]=3)[S:26][C:25]=2[CH:27]=[CH:28][CH:29]=1)=[O:32])=[O:42])([CH3:37])([CH3:36])[CH3:35]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 2-{5-chloro-2-[3-(4-methylpiperazin-1-yl)-propylamino]-pyrimidin-4-yl}-benzo[b]thiophene-4-carboxylic acid tri-hydrochloride (425 mg, 0.960 mmol), tert-butylcarbazate (398 mg, 3.01 mmol), diisopropylethylamine (0.500 mL, 2.87 mmol), (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (510 mg, 1.15 mmol), and lithium chloride (498 mg, 11.7 mmol) in DMF (6 mL) is heated at 50° C. for 20 hours. After cooling to room temperature, the solvent is removed and the residue is subjected to chromatography on silica gel, eluting with 2.0 M NH3/MeOH) in dichloromethane 0-10%, to give N′-(2-{5-chloro-2-[3-(4-methylpiperazin-1-yl)-propylamino]-pyrimidin-4-yl}-benzo[b]thiophene-4-carbonyl)-hydrazinecarboxylic acid tert-butyl ester (441 mg, 82% yield).

Workup

temperatureAfter cooling to room temperature
customthe solvent is removed
washeluting with 2.0 M NH3/MeOH) in dichloromethane 0-10%

Sources & evidence

ORD record: ord-72d4897d82574574af35fe2153a42208
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07547691B2

Reaction notes

Loading…