2-Methyl-3-butyn-2-ol → HCID 136068498, compound

HRID 2189241Notes

Reaction equation

HRID 2189241 reaction equation
BrC1C=C2C(=CC=1)N=C(C1C=CC=CC=1O)N=C2N[C@H]1CCN(C(OC(C)(C)C)=O)C1.[CH3:32][C:33]([OH:37])([CH3:36])[C:34]#[CH:35].Br[C:39]1[CH:40]=[C:41]2[C:46](=[CH:47][CH:48]=1)[N:45]=[C:44]([C:49]1[CH:54]=[C:53]([F:55])[CH:52]=[CH:51][C:50]=1[OH:56])[N:43]=[C:42]2[NH:57][C@H:58]1[CH2:62][CH2:61][N:60](C(OC(C)(C)C)=O)[CH2:59]1.OC1C=CC=CC=1C1N=C(N[C@H]2CCN(C(OC(C)(C)C)=O)C2)C2C(=CC=C(C#CCO)C=2)N=1>>[F:55][C:53]1[CH:52]=[CH:51][C:50]([OH:56])=[C:49]([C:44]2[N:43]=[C:42]([NH:57][C@H:58]3[CH2:62][CH2:61][NH:60][CH2:59]3)[C:41]3[C:46](=[CH:47][CH:48]=[C:39]([C:35]#[C:34][C:33]([OH:37])([CH3:36])[CH3:32])[CH:40]=3)[N:45]=2)[CH:54]=1

Participants

5

Reactant 4

HCID 82582-Methyl-3-butyn-2-olHCID 136068452HCID 136068452, compoundHCID 136068485HCID 136068485, compoundHCID 136337398HCID 136337398, compound

Product 1

HCID 136068498HCID 136068498, compound

Procedure

The title compound was prepared using a method analogous to that described in Synthesis 59, replacing propargyl alcohol and (S)-tert-butyl 3-(6-bromo-2-(2-hydroxyphenyl)quinazolin-4-ylamino)pyrrolidine-1-carboxylate with dimethyl propargyl alcohol and (S)-tert-butyl 3-(6-bromo-2-(5-fluoro-2-hydroxyphenyl)quinazolin-4-ylamino)pyrrolidine-1-carboxylate in Synthesis 59-A.

Workup

  1. customthat described in Synthesis 59

Sources & evidence

ORD record
ord-862a69939c84441d8507222a1d8017e2
Source dataset
uspto-grants-2012_12
Patent number
US08324226B2

Reaction notes

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