Morpholine → HCID 59553356, compound

HRID 1641226Notes

Reaction equation

HRID 1641226 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:27]=[C:28]([N:30]2[CH2:35][CH2:34][CH:33]([CH3:36])[CH2:32][CH2:31]2)[CH:29]=1)[C:5]([NH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([O:18][C:19]2[CH:24]=[CH:23][N:22]=[C:21](SC)[N:20]=2)=[CH:10][CH:9]=1)=[O:6].[NH:37]1[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1>>[F:1][C:2]1[CH:3]=[C:4]([CH:27]=[C:28]([N:30]2[CH2:35][CH2:34][CH:33]([CH3:36])[CH2:32][CH2:31]2)[CH:29]=1)[C:5]([NH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([O:18][C:19]2[CH:24]=[CH:23][N:22]=[C:21]([N:37]3[CH2:42][CH2:41][O:40][CH2:39][CH2:38]3)[N:20]=2)=[CH:10][CH:9]=1)=[O:6]

Participants

3

Reactant 2

HCID 8083MorpholineHCID 59553063HCID 59553063, compound

Product 1

HCID 59553356HCID 59553356, compound

Procedure

Compound is prepared from 3-fluoro-5-(4-methylpiperidin-1-yl)-N-(4-{[2-(methylthio)pyrimidin-4-yl]oxy}-1-naphthyl)benzamide (0.1 g, 0.2 mmol) and morpholine (10 mmol) according to conditions described in Step 4 of Example 3 and general procedure C. A pink solid is produced (15 mg). Mp: 88-89° C.; 1H NMR (300 MHz, CDCl3) δ 0.98(d, J=6.6 Hz, 3H), 1.25-1.38(m, 3H), 1.75 (d, J=12.6 Hz, 2H), 2.78-2.86(m, 2H), 3.64(s, 9H), 3.77(d, J=12 Hz, 1H), 6.07(d, J=5.7 Hz, 1H), 6.77(d, J=12 Hz, 1H), 6.98(d, J=7.8 Hz, 1H), 2.30-7.33(m, 2H), 7.49-7.60(m, 2H), 7.89-7.99(m, 3H), 8.13(s, 1H), 8.18(d, J=5.7 Hz, 1H); MS 542 (M+1).

Workup

  1. customA pink solid is produced (15 mg)

Sources & evidence

ORD record
ord-685272c0c1794644849439522f6fdd32
Source dataset
uspto-grants-2012_02
Patent number
US08114873B2

Reaction notes

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