tert-Butyl isocyanate → 4-({[(tert-Butylamino)carbonyl]amino}methyl)-2-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-1,3-thiazole-5-carboxylic acid

HRID 2234014Notes

Reaction equation

HRID 2234014 reaction equation
[NH2:1][CH2:2][C:3]1[N:4]=[C:5]([N:13]2[CH2:18][CH2:17][CH:16]([NH:19][C:20]([C:22]3[NH:23][C:24]([CH3:29])=[C:25]([Cl:28])[C:26]=3[Cl:27])=[O:21])[CH2:15][CH2:14]2)[S:6][C:7]=1[C:8]([O:10]CC)=[O:9].[C:30]([N:34]=[C:35]=[O:36])([CH3:33])([CH3:32])[CH3:31]>C(Cl)Cl>[C:30]([NH:34][C:35]([NH:1][CH2:2][C:3]1[N:4]=[C:5]([N:13]2[CH2:18][CH2:17][CH:16]([NH:19][C:20]([C:22]3[NH:23][C:24]([CH3:29])=[C:25]([Cl:28])[C:26]=3[Cl:27])=[O:21])[CH2:15][CH2:14]2)[S:6][C:7]=1[C:8]([OH:10])=[O:9])=[O:36])([CH3:33])([CH3:32])[CH3:31]

Participants

4

Reactant 2

HCID 62412tert-Butyl isocyanateHCID 68582554Ethyl 4-(aminomethyl)-2-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-1,3-thiazole-5-carboxylate

Product 1

HCID 685824304-({[(tert-Butylamino)carbonyl]amino}methyl)-2-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-1,3-thiazole-5-carboxylic acidYield 128.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 4-(aminomethyl)-2-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-1,3-thiazole-5-carboxylate (Example 246; 200 mg; 0.424 mmol) was dissolved in DCM (4 ml). tert-Butyl isocyanate (130 mg; 1.28 mmol) was added and the mixture stirred at room temperature for 1 h. The solvent was removed in vacuo and the ester (215 mg), LCMS:561 was treated with LiOH/THF in a manner analogous to Example 31 to give the title compound (290 mg).

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe ester (215 mg), LCMS:561 was treated with LiOH/THF in a manner analogous to Example 31

Sources & evidence

ORD record
ord-e806760e6dfc4194812910634ef04177
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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