Ammonia → HCID 178508476, compound

HRID 449052Notes

Reaction equation

HRID 449052 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]([C:30]([OH:32])=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.N.CC(O)C.C[N:39](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.CN(C=O)C>>[NH2:1][C:2]1[C:3]2[N:4]([C:8]([C@H:24]3[CH2:29][CH2:28][C@H:27]([C:30]([NH2:39])=[O:32])[CH2:26][CH2:25]3)=[N:9][C:10]=2[C:11]2[CH:12]=[CH:13][C:14]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:15][CH:16]=2)[CH:5]=[CH:6][N:7]=1

Participants

7

Reactant 6

HCID 222AmmoniaHCID 3776IsopropanolHCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178508478HCID 178508478, compound

Product 1

HCID 178508476HCID 178508476, compound

Procedure

A mixture trans-4-[8-amino-1-(4-phenoxyphenyl)-imidazo[1,5-a]pyrazin-3-yl]-cyclohexanecarboxylic acid (15.0 mg, 0.035 mmol), 2M of NH3 in i-PrOH (0.1 mL, 0.20 mmol), TBTU (22.5 mg, 0.070 mmol), DIEA (0.0647 mL, 0.371 mmol) and DMF (1 mL, 0.01 mol) was stirred at rt for 10 min. The reaction mixture was used for Gilson HPLC purification. The fractions containing the pure product were collected and concentrated in vacuo to afford the title compound as a yellow solid. 1H NMR (400 MHz, CDCl3): δ=1.63-1.76 (m, 2H), 1.78-1.90 (m, 2H), 2.08 (t, J=13.4 Hz, 4H), 3.00-3.10 (m, 1H) 6.94 (d, J=5.6 Hz, 1H), 7.10 (d, J=7.8 Hz, 2H), 7.15 (d, J=8.6 Hz, 2H), 7.20 (t, J=7.3 Hz, 1H), 7.36-7.44 (m, 3H), 7.58 (d, J=8.6 Hz, 2H). MS (ES+): m/z 427.96 (100) [MH+]. HPLC: tR=2.16 min (polar—5 min).

Workup

  1. customThe reaction mixture was used for Gilson HPLC purification
  2. additionThe fractions containing the pure product
  3. customwere collected
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d862083a6db04b56aad595b8a17edeb1
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

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