4-bromo-5-methoxy-N1-((2-(methylthio)benzo[d]thiazol-6-yl)methyl)benzene-1,2-diamine → (3aR,7aR)-3-(6-((9H-Purin-9-yl)methyl)benzo[d]thiazol-2-yl)-2,2-dimethyloctahydrobenzo[d]oxazole

HRID 1848016Notes

Reaction equation

HRID 1848016 reaction equation
[CH3:1][C:2]1([CH3:29])[N:6]([C:7]2[S:8][C:9]3[CH:15]=[C:14]([CH2:16][NH:17][C:18]4[C:23]([NH2:24])=[CH:22][N:21]=[CH:20][N:19]=4)[CH:13]=[CH:12][C:10]=3[N:11]=2)[C@@H:5]2[CH2:25][CH2:26][CH2:27][CH2:28][C@H:4]2[O:3]1.Br[C:31]1C=C(N)C(NCC2C=CC3N=C(SC)SC=3C=2)=CC=1OC>>[N:21]1[CH:22]=[C:23]2[C:18]([N:17]([CH2:16][C:14]3[CH:13]=[CH:12][C:10]4[N:11]=[C:7]([N:6]5[C@@H:5]6[CH2:25][CH2:26][CH2:27][CH2:28][C@H:4]6[O:3][C:2]5([CH3:29])[CH3:1])[S:8][C:9]=4[CH:15]=3)[CH:31]=[N:24]2)=[N:19][CH:20]=1

Participants

3

Reactant 2

HCID 866810304-bromo-5-methoxy-N1-((2-(methylthio)benzo[d]thiazol-6-yl)methyl)benzene-1,2-diamineHCID 86681037N4-((2-((3aR,7aR)-2,2-dimethylhexahydrobenzo[d]oxazol-3(2H)-yl)benzo[d]thiazol-6-yl)methyl)pyrimidine-4,5-diamine

Product 1

HCID 86681038(3aR,7aR)-3-(6-((9H-Purin-9-yl)methyl)benzo[d]thiazol-2-yl)-2,2-dimethyloctahydrobenzo[d]oxazole

Procedure

(3aR,7aR)-3-(6-((9H-Purin-9-yl)methyl)benzo[d]thiazol-2-yl)-2,2-dimethyloctahydrobenzo[d]oxazole was synthesized as an oil (220 mg) using a procedure analogous to that described in Step 3 of Example 41, substituting N4-((2-((3aR,7aR)-2,2-dimethylhexahydrobenzo[d]oxazol-3(2H)-yl)benzo[d]thiazol-6-yl)methyl)pyrimidine-4,5-diamine from Step 6 of this Example for 4-bromo-5-methoxy-N1-((2-(methylthio)benzo[d]thiazol-6-yl)methyl)benzene-1,2-diamine used in Example 41. LCMS (ESI) m/z 421 (M+H)+.

Sources & evidence

ORD record
ord-f2f564089fd448eeb99395f3f326ce32
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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