6-Chloro-4-(piperidin-4-ylamino)chromen-2-one → 4-(1-Benzooxazol-5-ylmethyl-piperidin-4-ylamino)-6-chloro-chromen-2-one

HRID 897251Notes

Reaction equation

HRID 897251 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7](=[O:12])[CH:6]=[C:5]2[NH:13][CH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.[O:20]1[C:24]2[CH:25]=[CH:26][C:27]([CH:29]=O)=[CH:28][C:23]=2[N:22]=[CH:21]1>>[O:20]1[C:24]2[CH:25]=[CH:26][C:27]([CH2:29][N:17]3[CH2:18][CH2:19][CH:14]([NH:13][C:5]4[C:4]5[C:9](=[CH:10][CH:11]=[C:2]([Cl:1])[CH:3]=5)[O:8][C:7](=[O:12])[CH:6]=4)[CH2:15][CH2:16]3)=[CH:28][C:23]=2[N:22]=[CH:21]1

Participants

3

Reactant 2

HCID 116376956-Chloro-4-(piperidin-4-ylamino)chromen-2-oneHCID 223483181,3-Benzoxazole-5-carbaldehyde

Product 1

HCID 115533164-(1-Benzooxazol-5-ylmethyl-piperidin-4-ylamino)-6-chloro-chromen-2-one

Procedure

6-Chloro-4-(piperidin-4-ylamino)-chromen-2-one and benzooxazole-5-carbaldehyde were allowed to react in a manner analogous to that previously described to give the title compound. 1H NMR (500 MHz, DMSO-D6) δ ppm 1.66 (m, 2H) 1.91 (m, 2H) 2.14 (m, J=10.29 Hz, 2H) 2.85 (m, 2H) 3.50 (m, 1H) 3.63 (s, 2H) 5.28 (s, 1H) 7.29 (m, 1H) 7.33 (m, 1H) 7.41 (m, 1H) 7.62 (m, 1H) 7.71 (m, 2H) 8.32 (m, 1H) 8.71 (s, 1H); MS (DCI/NH3) m/z 410 [M+H9 +.

Workup

  1. customto react in a manner analogous to

Sources & evidence

ORD record
ord-0b4b5363483a4f248348647242533799
Source dataset
uspto-grants-2005_07
Patent number
US06921821B2

Reaction notes

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