Hydrochloric Acid → HCID 67970448, compound

HRID 882023Notes

Reaction equation

HRID 882023 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][N:13]([C:16]3[N:21]=[C:20]4[N:22]([CH3:29])[C:23]5[CH2:28][CH2:27][NH:26][CH2:25][C:24]=5[C:19]4=[CH:18][CH:17]=3)[C:12](=[O:30])[CH:11]=2)=[N:6][CH:7]=1.[ClH:31]>CO>[ClH:31].[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][N:13]([C:16]3[N:21]=[C:20]4[N:22]([CH3:29])[C:23]5[CH2:28][CH2:27][NH:26][CH2:25][C:24]=5[C:19]4=[CH:18][CH:17]=3)[C:12](=[O:30])[CH:11]=2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57524507HCID 57524507, compound

Product 1

HCID 67970448HCID 67970448, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 4-((5-fluoropyridin-2-yl)methoxy)-1-(9-methyl-5,7,8,9-tetrahydro-6H-pyrido[3′,4′:4,5]pyrrolo[2,3-b]pyridin-2-yl)pyridin-2(1H)-one (75 mg, 0.18 mmol) in MeOH (2.0 mL) was treated with 1.25 M HCl in MeOH (0.15 mL, 0.18 mmol), and the resulting solution was stirred at ambient temperature for 2 h. The resulting solids were collected by filtration to provide the title compound (63 mg, 77%) as an off-white powder: 250-256° C. decomp.; 1H NMR (500 MHz, DMSO-d6) δ 8.62 (d, J=3.0 Hz, 1H), 7.97 (s, J=8.0 Hz, 1H), 7.87-7.78 (m, 2H), 7.69-7.64 (m, 1H), 7.30 (s, J=8.0 Hz, 1H), 7.09 (br s, 1H), 6.19 (dd, J=7.5, 2.5 Hz, 1H), 5.99 (d, J=3.0 Hz, 1H), 5.23 (s, 2H), 4.12 (s, 2H), 3.68 (s, 3H), 3.36-3.21 (m, 2H, overlap with H2O), 2.94 (t, J=5.5 Hz, 2H); ESI MS m/z 406 [M+H]+; HPLC (Method A)>99% (AUC), tR=11.4 min.

Workup

  1. filtrationThe resulting solids were collected by filtration

Sources & evidence

ORD record
ord-78f757c8dba64398822252cab1e9dd47
Source dataset
uspto-grants-2015_03
Patent number
US08993765B2

Reaction notes

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