Methanol → HCID 59593046, compound

HRID 2098858Notes

Reaction equation

HRID 2098858 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:5]2[S:10][C:9]([CH2:11][NH:12][CH3:13])=[CH:8][C:6]=2[N:7]=1.C([O:23][C:24]([CH3:29])([CH3:28])[C:25](Cl)=[O:26])(=O)C.CC1(C)C(C)(C)OB([C:38]2[CH:46]=[CH:45][CH:44]=[C:43]3[C:39]=2[CH:40]=[N:41][NH:42]3)O1.CO>C1COCC1>[NH:42]1[C:43]2[C:39](=[C:38]([C:2]3[N:3]=[C:4]([N:14]4[CH2:19][CH2:18][O:17][CH2:16][CH2:15]4)[C:5]4[S:10][C:9]([CH2:11][N:12]([CH3:13])[C:25](=[O:26])[C:24]([OH:23])([CH3:28])[CH3:29])=[CH:8][C:6]=4[N:7]=3)[CH:46]=[CH:45][CH:44]=2)[CH:40]=[N:41]1

Participants

6

Reactant 4

HCID 887MethanolHCID 1234962-Acetoxyisobutyroyl chlorideHCID 454801864-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazoleHCID 595929371-(2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)-N-methylmethanamine

Product 1

HCID 59593046HCID 59593046, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)-N-methylmethanamine 55 from Example 11a (0.22 g) was reacted with 2-acetoxyisobutyryl 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. The resulting compound was dissolved in 2 mL THF and 2 mL MeOH followed by the addition of 2 mL 1M liOH and the resulting solution stirred for 2.5 hours. Complete reaction was confirmed by LCMS and the reaction was concentrated in vacuo to give 80.2 mg of 407 after RP-HPLC purification (52% yield). MS (Q1) 467.2 (M)+

Workup

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

Sources & evidence

ORD record
ord-47349397000e458981adaf74dfc2978b
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

Loading…