Trifluoroacetic acid → HCID 22224743, compound

HRID 1635462Notes

Reaction equation

HRID 1635462 reaction equation
O[C:2]1([C:8]#[C:9][C:10]2[CH:29]=[CH:28][C:13]3[N:14]=[C:15]([C:20]4[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=4)[C:23]#[N:24])[CH2:16][C:17](=[O:19])[NH:18][C:12]=3[CH:11]=2)[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.IC1C=C(C2CC(=O)NC3C=C(C#CC4C=CC=CC=4)C=CC=3N=2)C=CC=1.C(C1(O)CCOCC1)#C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[O:5]1[CH2:4][CH:3]=[C:2]([C:8]#[C:9][C:10]2[CH:29]=[CH:28][C:13]3[N:14]=[C:15]([C:20]4[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=4)[C:23]#[N:24])[CH2:16][C:17](=[O:19])[NH:18][C:12]=3[CH:11]=2)[CH2:7][CH2:6]1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 155504854-Ethynyloxan-4-olHCID 22224695HCID 22224695, compoundHCID 222248983-[7-(4-hydroxy-tetrahydro-pyran-4-ylethynyl)-4-oxo-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl]-benzonitrile

Product 1

HCID 22224743HCID 22224743, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepared from 3-[7-(4-hydroxy-tetrahydro-pyran-4-ylethynyl)-4-oxo-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl]-benzonitrile [prepared from 4-(3-iodophenyl)-8-phenylethynyl-1,3-dihydro-benzo[b][1,4)diazepin-2-one (Example 11) (387 mg, 1.0 mmol) and 4-ethynyl-tetrahydro-pyran-4-ol [CAS-No. 57385-16-7] (315 mg, 2.5 mmol) according to the general procedure F. Obtained as a yellow solid (296 mg)] (50 mg, 0.13 mmol) by treatment with TFA in CH2Cl2 according to the general procedure M. Obtained as a light yellow solid (16 mg).

Sources & evidence

ORD record
ord-1782ccf67be8477e8bc897736f7dd384
Source dataset
uspto-grants-2003_01
Patent number
US06509328B1

Reaction notes

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