Triphenylphosphine → HCID 178430600, compound

HRID 226000Notes

Reaction equation

HRID 226000 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[C:14]([CH3:15])=[C:13]([N:16]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26](I)[CH:25]=3)C(OC(C)(C)C)=O)[N:12]3[N:31]=[CH:32][CH:33]=[C:11]3[N:10]=2)[CH2:4][CH2:3]1.[N:34]1[CH:39]=[CH:38][CH:37]=[C:36](B(O)O)[CH:35]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>>[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[C:14]([CH3:15])=[C:13]([NH:16][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:36]4[CH:35]=[N:34][CH:39]=[CH:38][CH:37]=4)[CH:25]=3)[N:12]3[N:31]=[CH:32][CH:33]=[C:11]3[N:10]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 3

HCID 11776TriphenylphosphineHCID 27343783-Pyridinylboronic acidHCID 178430601HCID 178430601, compound

Product 1

HCID 178430600HCID 178430600, compoundYield 15%

Procedure

The title compound and Boc protected intermediate were synthesised in the same manner as above using N-{5-[(trans-4-aminocyclohexyl)amino]-6-methyl(pyrazolo[1,5-a]pyrimidin-7-yl)}(tert-butoxy)-N-(3-iodophenyl)carboxamide, pyridine-3-boronic acid, Na2CO3 palladium (II) acetate and triphenylphosphine. The title compound (6.1 mg, 15% yield as 3 trifluoroacetic acids salt) was obtained. The HPLC retention time and ESI/MS data for this compound are shown below.

Workup

  1. customThe title compound and Boc protected intermediate were synthesised in the same manner as

Sources & evidence

ORD record
ord-38c7412816364a3889f87c36d0746461
Source dataset
uspto-grants-2009_07
Patent number
US07557110B2

Reaction notes

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