2,3-Difluorobenzoyl chloride → HCID 25002762, compound

HRID 1015350Notes

Reaction equation

HRID 1015350 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][O:8][C:9]2[CH:18]=[CH:17][CH:16]=[C:15]3[C:10]=2[C:11]([NH2:20])=[N:12][C:13]([NH2:19])=[N:14]3)[CH2:3][CH2:2]1.[F:21][C:22]1[C:30]([F:31])=[CH:29][CH:28]=[CH:27][C:23]=1[C:24](Cl)=[O:25]>>[NH2:19][C:13]1[N:12]=[C:11]([NH2:20])[C:10]2[C:15](=[CH:16][CH:17]=[CH:18][C:9]=2[O:8][CH2:7][CH:4]2[CH2:5][CH2:6][N:1]([C:24]([C:23]3[CH:27]=[CH:28][CH:29]=[C:30]([F:31])[C:22]=3[F:21])=[O:25])[CH2:2][CH2:3]2)[N:14]=1

Participants

3

Reactant 2

HCID 5195492,3-Difluorobenzoyl chlorideHCID 575765655-(Piperidin-4-ylmethoxy)quinazoline-2,4-diamine

Product 1

HCID 25002762HCID 25002762, compoundYield 74%

Procedure

The amidation of 5-(piperidin-4-ylmethoxy)quinazoline-2,4-diamine (50 mg; 0.18 mmol) was carried out using 2,3-difluorobenzoyl chloride (65 mg; 0.37 mmol) via Method AA to yield 114 mg. (74% yield). 1HNMR (400 MHz, DMSO-d6) δ 7.51 (q, J=8.8 Hz, 1H), 7.33 (m, 2H), 7.2 (m, 3H), 6.77 (d, J=8.4 Hz, 1H), 6.54 (d, J=8.0 Hz, 1H), 5.94 (br s, 2H), 4.54 (br d, J=12.8 Hz, 1H), 4.03 (d, J=6.0 Hz, 2H), 3.44 (d, J=14.0 Hz, 1H), 3.14 (t, J=12.4 Hz, 1H), 2.88 (m, 1H), 2.23 (s, 1H), 1.9 (d, J=12.4 Hz, 1H), 1.75 (d, J=10.8 Hz, 1H), 1.26 (m, 2H). MS m/z (ESI) 414 (M+H)+.

Workup

  1. customto yield 114 mg

Sources & evidence

ORD record
ord-cce05de9a8b24820b0f982d50043f641
Source dataset
uspto-grants-2011_07
Patent number
US07985755B2

Reaction notes

Loading…