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

HRID 969817Notes

Reaction equation

HRID 969817 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-3ac376ce4ec34f5eafd9a7966b6f65c7
Source dataset
uspto-grants-2007_12
Patent number
US07307094B2

Reaction notes

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