Hexachloroethane → HCID 58458920, compound

HRID 390347Notes

Reaction equation

HRID 390347 reaction equation
[CH2:1]([O:8][C:9]1[C:18](=[O:19])[N:17]2[C:12]([C:13]([CH3:21])([CH3:20])[O:14][CH2:15][CH2:16]2)=[N:11][C:10]=1[C:22]([NH:24][NH:25][C:26](=O)[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=1)=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCN(C(C)C)C(C)C.ClC(Cl)(Cl)C(Cl)(Cl)Cl>CC#N>[CH2:1]([O:8][C:9]1[C:18](=[O:19])[N:17]2[C:12]([C:13]([CH3:21])([CH3:20])[O:14][CH2:15][CH2:16]2)=[N:11][C:10]=1[C:22]1[O:23][C:26]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)=[N:25][N:24]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6214HexachloroethaneHCID 11776TriphenylphosphineHCID 81531DiisopropylethylamineHCID 67115353HCID 67115353, compound

Product 1

HCID 58458920HCID 58458920, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To stirred solution of 3-(benzyloxy)-N′-(2-(4-fluorophenyl)acetyl)-9,9-dimethyl-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carbohydrazide (0.075 g, 0.16 mmol), Ph3P (0.074 g, 0.28 mmol) and DIEA (0.16 mL, 0.91 mmol) in anhydrous CH3CN (3 mL) was added hexachloroethane (0.048 g, 0.20 mmol) all at once at room temperature. After 4 h, the resulting greenish-yellow reaction mixture was purified by preparative HPLC on a C18 column using water/MeOH containing 0.1% TFA as eluent to afford title compound (0.072 g, 86% yield) as a yellow solid. 1HNMR (500 MHz, CDCl3) δ: 7.42-7.40 (2H, m), 7.30-7.28 (3H, m), 7.24 (2H, dd, J=8.2, 5.55.34 (2H, s), 4.20 (2H, s), 4.07-4.01 (4H, m), 1.64 (6H, s). Hz)), 6.99 (2H, t, J=8.6 Hz), HRMS (M+H) calcd for C25H24N4O4F: 463.1782. found: 463.1788.

Workup

  1. customthe resulting greenish-yellow reaction mixture was purified by preparative HPLC on a C18 column

Sources & evidence

ORD record
ord-7efcb5f0677f4469aac92af4753aca87
Source dataset
uspto-grants-2013_02
Patent number
US08383639B2

Reaction notes

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