Methylamine → HCID 178484006, compound

HRID 449058Notes

Reaction equation

HRID 449058 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([C:8]([C@H:24]3[CH2:29][CH2:28][C@H:27]([CH2:30]OS(C4C=CC(C)=CC=4)(=O)=O)[CH2:26][CH2:25]3)=[N:9][C:10]=2[C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:13][CH:12]=2)[CH:5]=[CH:6][N:7]=1.[CH3:42][NH2:43]>CO>[CH3:42][NH:43][CH2:30][C@H:27]1[CH2:28][CH2:29][C@H:24]([C:8]2[N:4]3[CH:5]=[CH:6][N:7]=[C:2]([NH2:1])[C:3]3=[C:10]([C:11]3[CH:12]=[CH:13][C:14]([O:17][C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)=[CH:15][CH:16]=3)[N:9]=2)[CH2:25][CH2:26]1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 178427749HCID 178427749, compound

Product 1

HCID 178484006HCID 178484006, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of trans-toluene-4-sulfonic acid 4-[8-amino-1-(4-phenoxyphenyl)-imidazo[1,5-a]pyrazin-3-yl]-cyclohexylmethyl ester (15.0 mg, 0.0264 mmol), 2.0 M of methylamine in MeOH (0.5 mL) and MeOH (2 mL) was microwaved at 300 watt, 100° C. for 1 h. The material was concentrated and purified by a prep TLC plate, eluting with 8% (7N NH3 in MeOH) in DCM, to afford the title compound as an off-white solid. 1H NMR (400 MHz, CDCl3): δ 1.10-1.22 (m, 2H), 1.60-1.69 (m, 1H), 1.81-1.95 (m, 2H), 1.97-2.03 (m, 2H), 2.10 (d, J=11.4 Hz, 2H), 2.46 (s, 3H), 2.51 (d, J=6.6 Hz, 2H), 2.87-2.97 (m, 1H), 5.09 (br. s., 2H), 7.04-7.18 (m, 6H), 7.23 (d, J=5.1 Hz, 1H), 7.34-7.41 (m, 2H), 7.59-7.66 (m, 2H). MS (ES+): m/z 427.89 (100) [MH+]. HPLC: tR=1.89 min (polar—5 min).

Workup

  1. concentrationThe material was concentrated
  2. custompurified by a prep TLC plate
  3. washeluting with 8% (7N NH3 in MeOH) in DCM

Sources & evidence

ORD record
ord-20583f4a3f3b4e888c1643408f1cc460
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

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