6-Bromopyridin-3-amine → N-(1-(4-(5-aminopyridin-2-yl)cyclohexyl)azetidin-3-yl)-2-((6-(trifluoromethyl)quinazolin-4-yl)amino)acetamide

HRID 2175580Notes

Reaction equation

HRID 2175580 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]2)=[N:6][CH:7]=1.BrC1N=CC(N)=CC=1.CC1(C)C(C)(C)OB(C2CCC3(OCCO3)CC=2)O1.[NH:42]1[CH2:45][CH:44]([NH:46][C:47](=[O:64])[CH2:48][NH:49][C:50]2[C:59]3[C:54](=[CH:55][CH:56]=[C:57]([C:60]([F:63])([F:62])[F:61])[CH:58]=3)[N:53]=[CH:52][N:51]=2)[CH2:43]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:13][CH2:12][CH:11]([N:42]3[CH2:43][CH:44]([NH:46][C:47](=[O:64])[CH2:48][NH:49][C:50]4[C:59]5[C:54](=[CH:55][CH:56]=[C:57]([C:60]([F:61])([F:63])[F:62])[CH:58]=5)[N:53]=[CH:52][N:51]=4)[CH2:45]3)[CH2:10][CH2:9]2)=[N:6][CH:7]=1

Participants

6

Reactant 5

HCID 6428116-Bromopyridin-3-amineHCID 36970768-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1,4-dioxaspiro(4.5)dec-7-eneHCID 5049666Sodium triacetoxyborohydrideHCID 680033544-(5-Aminopyridin-2-yl)cyclohexanoneHCID 68003594N-(azetidin-3-yl)-2((6-(trifluoromethyl)quinazolin-4-yl)amino)acetamide

Product 1

HCID 54772207N-(1-(4-(5-aminopyridin-2-yl)cyclohexyl)azetidin-3-yl)-2-((6-(trifluoromethyl)quinazolin-4-yl)amino)acetamide

Procedure

Reaction of 4-(5-aminopyridin-2-yl)cyclohexanone (prepared by the reaction of 6-bromopyridin-3-amine with 8-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,4-dioxa-spiro[4.5]dec-7-ene using the sequence described in Example 1 Step A-C) with N-(azetidin-3-yl)-2-((6-(trifluoromethyl)quinazolin-4-yl)amino)acetamide (as prepared in Example 1 Step G) in the presence of TEA and NaBH(OAc)3 as described in Example 1, Step H afforded the product.

Workup

  1. customafforded the product

Sources & evidence

ORD record
ord-b99c57609dce404c948ef18e5f626e6b
Source dataset
uspto-grants-2015_06
Patent number
US09062048B2

Reaction notes

Loading…