4-(Carbamoylamino)benzeneboronic acid, pinacol ester → (S)-1-(4-(6-(cyclopropylmethyl)-4-(3-methylmorpholino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)phenyl)urea

HRID 1626560Notes

Reaction equation

HRID 1626560 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][C@@H:16]2[CH3:21])[C:5]2[CH2:10][N:9]([CH2:11][CH:12]3[CH2:14][CH2:13]3)[CH2:8][C:6]=2[N:7]=1.CC1(C)C(C)(C)OB([C:30]2[CH:35]=[CH:34][C:33]([NH:36][C:37]([NH2:39])=[O:38])=[CH:32][CH:31]=2)O1>>[CH:12]1([CH2:11][N:9]2[CH2:10][C:5]3[C:4]([N:15]4[CH2:20][CH2:19][O:18][CH2:17][C@@H:16]4[CH3:21])=[N:3][C:2]([C:30]4[CH:35]=[CH:34][C:33]([NH:36][C:37]([NH2:39])=[O:38])=[CH:32][CH:31]=4)=[N:7][C:6]=3[CH2:8]2)[CH2:14][CH2:13]1

Participants

3

Reactant 2

HCID 167274404-(Carbamoylamino)benzeneboronic acid, pinacol esterHCID 86663153(S)-4-(2-chloro-6-(cyclopropylmethyl)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)-3-methylmorpholine

Product 1

HCID 46912496(S)-1-(4-(6-(cyclopropylmethyl)-4-(3-methylmorpholino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)phenyl)urea

Procedure

Method as described for example 47 using intermediate 8 and 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea as starting materials. Purified by prep. LCMS (high pH) and (low pH).

Workup

  1. customPurified by prep

Sources & evidence

ORD record
ord-d224a5549ec2406daea362d311230dd2
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

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