Isopropyl isocyanate → HCID 57725391, compound

HRID 1922236Notes

Reaction equation

HRID 1922236 reaction equation
[CH3:1][NH:2][C:3](=[O:27])[C:4]1[CH:9]=[C:8]([O:10][C:11]2[CH:26]=[CH:25][C:14]3[N:15]=[C:16]([NH:18][C@H:19]4[CH2:24][CH2:23][CH2:22][NH:21][CH2:20]4)[S:17][C:13]=3[CH:12]=2)[CH:7]=[CH:6][N:5]=1.CCN(C(C)C)C(C)C.[N:37]([CH:40]([CH3:42])[CH3:41])=[C:38]=[O:39]>CN1C(=O)CCC1>[CH:40]([NH:37][C:38]([N:21]1[CH2:22][CH2:23][CH2:24][C@H:19]([NH:18][C:16]2[S:17][C:13]3[CH:12]=[C:11]([O:10][C:8]4[CH:7]=[CH:6][N:5]=[C:4]([C:3]([NH:2][CH3:1])=[O:27])[CH:9]=4)[CH:26]=[CH:25][C:14]=3[N:15]=2)[CH2:20]1)=[O:39])([CH3:42])[CH3:41]

Participants

5

Reactant 3

HCID 61277Isopropyl isocyanateHCID 81531DiisopropylethylamineHCID 57725452HCID 57725452, compound

Product 1

HCID 57725391HCID 57725391, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To the solution of (S)—N-methyl-4-(2-(piperidin-3-ylamino)benzo[d]thiazol-6-yloxy)picolinamide (13 mg, 30 μmol) and DIPEA (17 μL, 100 μmol) in 300 μL of NMP was added 2-isocyanatopropane (5 μL, 50 μmol). The reaction solution was stirred at room temperature for 18 hours. The crude reaction solution was purified on prep HPLC and evaporated in vacuo to give (S)-4-(2-(1-(isopropylcarbamoyl)piperidin-3-ylamino)benzo[d]thiazol-6-yloxy)-N-methylpicolinamide (5.9 mg, 12 μmol) as white powder. ES/MS m/z 469.2 (MH+).

Workup

  1. customThe crude reaction solution
  2. customwas purified on prep HPLC
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-fcb712ba879b45beb787618637ec43e0
Source dataset
uspto-grants-2012_05
Patent number
US08173689B2

Reaction notes

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