Acetyl chloride → HCID 59593006, compound

HRID 2098859Notes

Reaction equation

HRID 2098859 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[C:5]2[S:10][C:9]([CH2:11][NH:12][CH3:13])=[C:8]([CH3:14])[C:6]=2[N:7]=1.[C:21](Cl)(=[O:23])[CH3:22].CC1(C)C(C)(C)OB([C:33]2[CH:41]=[CH:40][CH:39]=[C:38]3[C:34]=2[CH:35]=[N:36][NH:37]3)O1>>[NH:37]1[C:38]2[C:34](=[C:33]([C:2]3[N:3]=[C:4]([N:15]4[CH2:20][CH2:19][O:18][CH2:17][CH2:16]4)[C:5]4[S:10][C:9]([CH2:11][N:12]([CH3:13])[C:21](=[O:23])[CH3:22])=[C:8]([CH3:14])[C:6]=4[N:7]=3)[CH:41]=[CH:40][CH:39]=2)[CH:35]=[N:36]1

Participants

4

Reactant 3

HCID 6367Acetyl chlorideHCID 454801864-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazoleHCID 59817854(2-chloro-7-methyl-4-morpholinothieno[3,2-d]pyrimidin-6-yl)-N-methylmethanamine

Product 1

HCID 59593006HCID 59593006, compoundYield 40%

Procedure

1-(2-Chloro-7-methyl-4-morpholinothieno[3,2-d]pyrimidin-6-yl)-N-methylmethanamine 56 from Example 11b was reacted with acetyl chloride (1.2 eq) followed by Suzuki coupling of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)1H-indazole 7 as per General Procedure K. Complete reaction was confirmed by LCMS and the reaction was concentrated in vacuo to give 101.9 mg of 408 after RP-HPLC purification (40% yield). MS (Q1) 437.2 (M)+.

Workup

  1. customComplete reaction
  2. concentrationthe reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-bacfdfb318bb40f5a6a78728cdb5d4a1
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

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