4-Amino-1-Boc-piperidine → HCID 11602208, compound

HRID 506230Notes

Reaction equation

HRID 506230 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[C:15]1([C:21]2[O:22][C:23]3[C:24](=[C:26]([C:30]([OH:32])=[O:31])[CH:27]=[CH:28][CH:29]=3)[N:25]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>FC(F)(F)C(O)=O.O>[C:11]([O:10][C:8]([N:5]1[CH2:4][CH2:3][CH:2]([NH:1][C:30]([C:26]2[CH:27]=[CH:28][CH:29]=[C:23]3[O:22][C:21]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)=[N:25][C:24]=23)=[O:31])[CH2:7][CH2:6]1)=[O:9])([CH3:14])([CH3:13])[CH3:12].[NH:5]1[CH2:6][CH2:7][CH:2]([NH:1][C:30]([C:26]2[CH:27]=[CH:28][CH:29]=[C:23]3[O:22][C:21]([C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=4)=[N:25][C:24]=23)=[O:32])[CH2:3][CH2:4]1

Participants

6

Reactant 2

HCID 12682914-Amino-1-Boc-piperidineHCID 108683692-Phenylbenzoxazole-4-carboxylic acid

Product 2

HCID 11602208HCID 11602208, compoundYield 74%HCID 68459083HCID 68459083, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

N-(1-tert-butyloxycarbonylpiperidin-4-yl)-2-phenylbenzoxazole-4-carboxamide was prepared from 4-amino-1-tert-butyloxycarbonylpiperidine and 2-phenylbenzoxazole-4-carboxylic acid using the coupling method described in Step C of Example 7. This crude material was immediately dissolved in a mixture of trifluoroacetic acid (1.0 mL) and water (0.05 mL) and the resulting solution stirred at ambient temperature for 0.5 hours. The reaction was then concentrated to dryness in vacuo. The resulting oil was purified using preparative HPLC to afford a 74% yield of N-(piperidin-4-yl)-2-phenylbenzoxazole-4-carboxamide as a white solid: mp 99-102° C.; 1H NMR (500 MHz, CD3OD) δ 8.27 (dd, J=7.5, 2.0 Hz, 2H), 7.89 (dd, J=8.0, 1.0 Hz, 1H), 7.78 (d, J=8.0 Hz, 1H), 7.65-7.58 (m, 3H), 7.49 (t, J=8.0 Hz, 1H), 4.20-4.14 (m, 1H), 3.26 (d, J=13.0 Hz, 2H), 2.90 (t, J=12.0 Hz, 2H), 2.16 (d, J=12.5 Hz, 2H), 1.75 (q, J=12.5 Hz, 2H); MS (ESI) m/z 322 [M+H]+.

Workup

  1. concentrationThe reaction was then concentrated to dryness in vacuo
  2. customThe resulting oil was purified

Sources & evidence

ORD record
ord-8651e73b0f6b4ef4ad3b1c08011ffd16
Source dataset
uspto-grants-2010_08
Patent number
US07781430B2

Reaction notes

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