tert-Butyl carbazate → HCID 15751505, compound

HRID 1974638Notes

Reaction equation

HRID 1974638 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:15]([F:32])=[CH:16][C:17]3[N:21]=[C:20]([CH2:22][C:23](OCC)=[O:24])[N:19]([CH:28]4[CH2:30][CH2:29]4)[C:18]=3[CH:31]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:33]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])(=[O:36])[NH:34][NH2:35]>N1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[C:15]([F:32])=[CH:16][C:17]3[N:21]=[C:20]([CH2:22][C:23]([NH:35][NH:34][C:33]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])=[O:24])[N:19]([CH:28]4[CH2:29][CH2:30]4)[C:18]=3[CH:31]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 70091tert-Butyl carbazateHCID 15751497HCID 15751497, compound

Product 1

HCID 15751505HCID 15751505, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Ethyl 6-[4-(tert-butoxycarbonyl)-1-piperazinyl]1-cyclopropyl-5-fluoro-2-benzimidazoleacetate (1.8 g, 4 mmol; from Example 2d) and tert.butyl carbazate (21 g, 16 mmol) are dissolved in pyridine (40 ml) and stirred at 115° under argon for 65 hours. The reaction solution is concentrated and triturated with 50 ml of ether. The separated product is filtered off under suction and dried. There is obtained tert-butyl 3-[[6-[4-(tert-butoxycarbonyl)-1-piperazinyl]-1-cyclopropyl-5-fluoro-2-benzimidazolyl]acetyl]carbazate. Yield: 0.49 g (23%); m.p. 202°-203°.

Workup

  1. concentrationThe reaction solution is concentrated
  2. customtriturated with 50 ml of ether
  3. filtrationThe separated product is filtered off under suction
  4. customdried

Sources & evidence

ORD record
ord-ab17f81c1cac4cfd8978738e9f32421f
Source dataset
uspto-grants-1994_02
Patent number
US05283248

Reaction notes

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