Isopropylamine → HCID 67418213, compound

HRID 2373928Notes

Reaction equation

HRID 2373928 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]2[N:16]=[C:17]([CH:25]3[CH2:28][CH2:27][CH2:26]3)[N:18]3[CH:23]=[CH:22][N:21]=[C:20](Cl)[C:19]=23)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:29]([NH2:32])([CH3:31])[CH3:30].CN1C(=[O:39])CCC1>>[CH:9]([OH:8])=[O:39].[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]2[N:16]=[C:17]([CH:25]3[CH2:28][CH2:27][CH2:26]3)[N:18]3[CH:23]=[CH:22][N:21]=[C:20]([NH:32][CH:29]([CH3:31])[CH3:30])[C:19]=23)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6363IsopropylamineHCID 13387N-methyl-2-pyrrolidoneHCID 59852760HCID 59852760, compound

Product 1

HCID 67418213HCID 67418213, compoundYield 36%

Procedure

To a solution of 1-(3-benzyloxy-phenyl)-8-chloro-3-cyclobutyl-imidazo[1,5-a]pyrazine (30 mg, 0.075 mmol) in NMP (0.4 ml) was added isopropylamine (44 mg, 0.75 mmol). The reaction was irradiated in the microwave (200 W, 150° C., 5 min.) and then poured onto water (10 ml) and extracted with EtOAc (2×10 ml). The combined organics were washed with brine (3×10 ml), dried (MgSO4), filtered and evaporated to dryness. Purification by mass-directed HPLC gave [1-(3-Benzyloxy-phenyl)-3-cyclobutyl-imidazo[1,5-a]pyrazin-8-yl]-isopropyl-amine formic acid salt (11.0 mg, 36%) as a colorless solid: 1H NMR (400 MHz, CD3OD) δ 8.21 (s, 1H), 7.49 (d, 3H, J=8.2 Hz), 7.44-7.31 (m, 4H), 7.29 (s, 1H), 7.24-7.17 (m, 2H), 7.04 (d, 1H, J=5.1 Hz), 5.21 (s, 2H), 4.24-4.11 (m, 1H), 4.04-3.94 (m, 1H), 2.64-2.47 (m, 4H), 2.28-2.17 (m, 1H), 2.10-2.01 (m, 1H), 1.14 (d, 6H, J=6.7 Hz), 1H not observed (NH); LCMS (ES+) m/z 413.21 [MH+] at Rt 3.40 min.

Workup

  1. customThe reaction was irradiated in the microwave (200 W, 150° C., 5 min.)
  2. additionpoured onto water (10 ml)
  3. extractionextracted with EtOAc (2×10 ml)
  4. washThe combined organics were washed with brine (3×10 ml)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customPurification by mass-directed HPLC

Sources & evidence

ORD record
ord-ca4cda4f56894d5186c4efddd2e96200
Source dataset
uspto-grants-2008_12
Patent number
US07459554B2

Reaction notes

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