Methanesulfonic Acid → HCID 86713641, compound

HRID 1430490Notes

Reaction equation

HRID 1430490 reaction equation
[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[NH2:6][C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([C:20]3[C:21]([Cl:37])=[CH:22][C:23]([F:36])=[C:24]([NH:26][C:27]([NH:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[O:28])[CH:25]=3)[C:13](=[O:19])[N:14]2[CH2:17][CH3:18])=[CH:9][N:8]=1>C(Cl)Cl.CC#N.O>[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[NH2:6][C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([C:20]3[C:21]([Cl:37])=[CH:22][C:23]([F:36])=[C:24]([NH:26][C:27]([NH:29][C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)=[O:28])[CH:25]=3)[C:13](=[O:19])[N:14]2[CH2:17][CH3:18])=[CH:9][N:8]=1

Participants

6

Reactant 2

HCID 6395Methanesulfonic AcidHCID 71584872HCID 71584872, compound

Product 1

HCID 86713641HCID 86713641, compoundYield 97%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent2×

Procedure

A 25 mg/mL solution of methanesulfonic acid in DCM (0.424 mL, 0.110 mmol) was added to a solution of 1-(5-(7-amino-1-ethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-4-chloro-2-fluorophenyl)-3-phenylurea (45 mg, 0.100 mmol) in DCM (4 mL), the mixture stirred for 15 min. and then evaporated at reduced pressure to give a solid. The solid was dissolved in MeCN and water, frozen, and lyophilized to give 1-(5-(7-amino-1-ethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-4-chloro-2-fluorophenyl)-3-phenylurea methanesulfonate (1.4 equiv.) (53 mg, 97% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.12 (s, 1H), 8.76 (s, 1H), 8.56 (s, 1H), 8.21 (d, 1H), 7.92 (s, 1H), 7.90 (br s, 2H), 7.60-7.56 (m, 1H), 7.42-7.40 (m, 2H), 7.28-7.24 (m, 2H), 6.98-6.95 (m, 1H), 6.74 (s, 1H), 4.12 (q, 2H), 2.34 (s, ˜4H), 1.23 (t, 3H); MS (ES-API) m/z: 452.1 [M+H]+.

Workup

  1. customevaporated at reduced pressure
  2. customto give a solid

Sources & evidence

ORD record
ord-c2a56197fcb74c8e98ab68dac7ba1af5
Source dataset
uspto-grants-2015_01
Patent number
US08940756B2

Reaction notes

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