tert-Butyl (3-aminopropyl)carbamate → N-(3-aminopropyl)-N-(4-(benzofuran-2-yl)thiazol-2-yl)thiophene-2-carboxamide

HRID 1713978Notes

Reaction equation

HRID 1713978 reaction equation
C(OC(=O)NCCCN)(C)(C)C.[O:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[CH:15]=[C:14]1[C:22]1[N:23]=[C:24]([N:27]([CH2:35][CH2:36][CH2:37][NH:38]C(=O)OC(C)(C)C)[C:28]([C:30]2[S:31][CH:32]=[CH:33][CH:34]=2)=[O:29])[S:25][CH:26]=1.C(O)(C(F)(F)F)=O.ClCCl>>[NH2:38][CH2:37][CH2:36][CH2:35][N:27]([C:24]1[S:25][CH:26]=[C:22]([C:14]2[O:13][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[CH:15]=2)[N:23]=1)[C:28]([C:30]1[S:31][CH:32]=[CH:33][CH:34]=1)=[O:29]

Participants

4

Reactant 3

HCID 2735700tert-Butyl (3-aminopropyl)carbamateHCID 21863450Trifluoroacetic acid methylene chlorideHCID 68407451HCID 68407451, compound

Product 1

HCID 68407996N-(3-aminopropyl)-N-(4-(benzofuran-2-yl)thiazol-2-yl)thiophene-2-carboxamide

Procedure

According to the procedure in Example 19, (3-amino-propyl)carbamic acid tert-butyl ester was transformed into tert-butyl 3-(N-(4-(benzofuran-2-yl)thiazol-2-yl)thiophene-2-carboxamido)propylcarbamate, which was reacted with TFA/dichoromethane (3:2), stirred at room temperature for 30 min, concentrated in vacuo, then dissolved in MeOH and treated with 1M HCl/ether. The resulting precipitate was filtered and dried in vacuo to provide N-(3-aminopropyl)-N-(4-(benzofuran-2-yl)thiazol-2-yl)thiophene-2-carboxamide (220 mg) as a white solid.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutiondissolved in MeOH
  3. additiontreated with 1M HCl/ether
  4. filtrationThe resulting precipitate was filtered
  5. customdried in vacuo

Sources & evidence

ORD record
ord-2eb6e81c8260488bb5345d6981069c9b
Source dataset
uspto-grants-2010_09
Patent number
US07795290B2

Reaction notes

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