Phosphorus oxychloride → HCID 135497093, compound

HRID 2373921Notes

Reaction equation

HRID 2373921 reaction equation
C(OP(N)(=O)[O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[C:15]([CH:23]3[CH2:26][CH2:25][CH2:24]3)[N:16]3[CH:21]=[CH:20][N:19]=[C:18](Cl)[C:17]=23)=[CH:9][C:8]=1[O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)(C)C.C(OC1C=C(C(NC(C2CCC2)=O)C2C(Cl)=NC=C[N:63]=2)C=CC=1OCC1C=CC(OC)=CC=1)C1C=CC=CC=1.O=P(Cl)(Cl)Cl>>[NH2:63][C:18]1[C:17]2[N:16]([C:15]([CH:23]3[CH2:24][CH2:25][CH2:26]3)=[N:14][C:13]=2[C:10]2[CH:11]=[CH:12][C:7]([OH:6])=[C:8]([O:27][CH2:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH:9]=2)[CH:21]=[CH:20][N:19]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 59852736HCID 59852736, compoundHCID 86604619HCID 86604619, compound

Product 1

HCID 135497093HCID 135497093, compound

Procedure

Phosphoramidic acid 2-benzyloxy-4-(8-chloro-3-cyclobutylimidazo[1,5-a]pyrazin-1-yl)-phenyl ester isopropyl ester: Followed General Cyclization described in Example 92-(a) whereby Cyclobutanecarboxylic acid [[3-benzyloxy-4-(4-methoxybenzyloxy)-phenyl]-(3-chloropyrazin-2-yl)-methyl]-amide was treated with POCl3 and then quenched with 2N NH3 in iPrOH to afford the title compound; 1H NMR (CDCl3, 400 MHz) δ 1.31 (d, 3H, J=6.0 Hz), 1.35 (d, 3H, J=6.4 Hz), 2.01-2.26 (m, 2H), 2.47-2.69 (m, 4H), 3.02 (d, 2H, J=4.0 Hz), 3.84 (quintet, 1H, J=8.4 Hz), 4.78 (septet, 1H, J=6.1 Hz), 5.17 (s, 2H), 7.27-7.53 (m, 10H); MS (ES): 526.9/528.9 (M/M+2).

Workup

  1. customquenched with 2N NH3 in iPrOH

Sources & evidence

ORD record
ord-a49eb59fe2534b9285a725f16d43d393
Source dataset
uspto-grants-2008_12
Patent number
US07459554B2

Reaction notes

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