Diisopropylethylamine → HCID 117683803, compound

HRID 1507516Notes

Reaction equation

HRID 1507516 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[S:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)=[C:6](Cl)[N:5]=[C:4]([CH:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[N:3]=1.[NH2:24][C@@H:25]1[CH2:30][CH2:29][CH2:28][N:27]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:26]1.C(N(CC)C(C)C)(C)C>C(O)C>[S:9]1[C:10]2[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=2[N:12]=[C:8]1[C:7]1[C:6]([NH:24][C@@H:25]2[CH2:30][CH2:29][CH2:28][N:27]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:26]2)=[N:5][C:4]([CH:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[N:3][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1501974tert-butyl (3R)-3-aminopiperidine-1-carboxylateHCID 89554257HCID 89554257, compound

Product 1

HCID 117683803HCID 117683803, compoundYield 78.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Following the same procedure as in step 4 of Example 21 using 2-[4,6-dichloro-2-(oxan-4-yl)pyrimidin-5-yl]-1,3-benzothiazole (90 mg, 0.25 mmol, 1.00 equiv), tert-butyl (3R)-3-aminopiperidine-1-carboxylate (49 mg, 0.24 mmol, 1.00 equiv), and N,N-Diisopropylethylamine (63 mg, 0.49 mmol, 1.98 equiv) in ethanol (2 mL). The reaction mixture was concentrated under reducing pressure to afford 100 mg of the title compound as a yellow solid, which was used directly for next step without further purification. 1H-NMR (CDCl3, 400 MHz,): δ ppm 1.29 (s, 9H), 1.73 (s, 1H), 1.90-2.08 (m, 8H), 2.98 (m, 8H), 3.00 (m, 1H), 3.30-4.48 (m, 10H), 7.33-7.50 (m, 2H), 7.46-8.06 (m, 4H), 11.09 (d, J=6.8, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-340e683b19d4439ba7ce19babfc93af3
Source dataset
uspto-grants-2015_12
Patent number
US09221809B2

Reaction notes

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