(6-fluoro-4H-1,3-benzodioxin-8-yl)methylamine → HCID 58603442, compound

HRID 2386339Notes

Reaction equation

HRID 2386339 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]3[CH:26]=[CH:25][N:24]=[C:23](Cl)[N:22]=3)[CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[F:28][C:29]1[CH:30]=[C:31]([CH2:39][NH2:40])[C:32]2[O:37][CH2:36][O:35][CH2:34][C:33]=2[CH:38]=1>>[F:28][C:29]1[CH:30]=[C:31]([CH2:39][NH:40][C:23]2[N:22]=[C:21]([C:17]3[CH:18]=[CH:19][CH:20]=[C:15]([NH:14][CH:11]4[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]4)[CH:16]=3)[CH:26]=[CH:25][N:24]=2)[C:32]2[O:37][CH2:36][O:35][CH2:34][C:33]=2[CH:38]=1

Participants

3

Reactant 2

HCID 2779911(6-fluoro-4H-1,3-benzodioxin-8-yl)methylamineHCID 866032444-[3-(2-Chloro-pyrimidin-4-yl)-phenylamino]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 58603442HCID 58603442, compound

Procedure

Intermediate 7 was coupled with C-(6-fluoro-4H-benzo[1,3]dioxin-8-yl)-methylamine following procedure F and the resulting intermediate 4eprotected following procedure G. LC-MS showed the product had the expected M+H+ of 436. 1H NMR (Varian 300 MHz, DMSO-d6, shifts relative to the solvent peak at 2.49 ppm) δ 8.6 (s, 1H) 8.4 (d, 1H) 8.3 (d, 1H) 7.8 (t, 1H) 7.4 (d, 1H), 7.2 (d, 1H), 7.1 (d, 2H), 6.6 (d, 2H), 3.4 (d, 2H), 2.8 (d, 2H).

Sources & evidence

ORD record
ord-cb7e8778705b438789eeaae14a1b9954
Source dataset
uspto-grants-2012_09
Patent number
US08268822B2

Reaction notes

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