Hydrochloric Acid → (s)-5-(6-((4-(2-Hydroxypropanoyl)piperazin-1-yl)methyl)-7-methyl-4-morpholinothieno[3,2-d]pyrimidin-2-yl)picolinonitrile

HRID 391122Notes

Reaction equation

HRID 391122 reaction equation
ClC1N=C(N2CCOCC2)C2SC(CN3CCN(C(OC(C)(C)C)=O)CC3)=C(C)C=2N=1.Cl.[CH3:33][C:34]1[C:38]2[N:39]=[C:40]([C:49]3[CH:50]=[CH:51][C:52]([C:55]#[N:56])=[N:53][CH:54]=3)[N:41]=[C:42]([N:43]3[CH2:48][CH2:47][O:46][CH2:45][CH2:44]3)[C:37]=2[S:36][C:35]=1[CH2:57][N:58]1[CH2:63][CH2:62][NH:61][CH2:60][CH2:59]1.[C:64](O)(=[O:68])[C@H:65]([CH3:67])[OH:66]>>[OH:66][C@@H:65]([CH3:67])[C:64]([N:61]1[CH2:60][CH2:59][N:58]([CH2:57][C:35]2[S:36][C:37]3[C:42]([N:43]4[CH2:48][CH2:47][O:46][CH2:45][CH2:44]4)=[N:41][C:40]([C:49]4[CH:50]=[CH:51][C:52]([C:55]#[N:56])=[N:53][CH:54]=4)=[N:39][C:38]=3[C:34]=2[CH3:33])[CH2:63][CH2:62]1)=[O:68]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 107689L-Lactic AcidHCID 56648760Tert-butyl 4-((2-chloro-7-methyl-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl)piperazine-1-carboxylateHCID 669340485-(7-Methyl-4-morpholino-6-((piperazin-1-yl)methyl)thieno[3,2-d]pyrimidin-2-yl)pyridine-2-carbonitrile

Product 1

HCID 24945990(s)-5-(6-((4-(2-Hydroxypropanoyl)piperazin-1-yl)methyl)-7-methyl-4-morpholinothieno[3,2-d]pyrimidin-2-yl)picolinonitrile

Procedure

Tert-butyl 4-((2-chloro-7-methyl-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl)piperazine-1-carboxylate (75 mg) was reacted with 6-cyanopyridin-3-yl-3-boronic ester via General Procedure A. This crude intermediate was subjected to General Procedure D in which the crude HCl salt of 5-(7-methyl-4-morpholino-6-((piperazin-1-yl)methyl)thieno[3,2-d]pyrimidin-2-yl)pyridine-2-carbonitrile was reacted with L-Lactic acid via General Procedure B to give 8.6 mg of 405 after reverse phase HPLC purification. MS (Q1) 508.2 (M)+.

Sources & evidence

ORD record
ord-c2cbada42dc64b66bacea233c9257d3c
Source dataset
uspto-grants-2013_02
Patent number
US08383620B2

Reaction notes

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