m-Formylbenzonitrile → HCID 135886519, compound

HRID 2424828Notes

Reaction equation

C[C@@H]1CN(CC2C=NC(C)=NC=2)C[C@H]1C1NC(=O)C2C=NN(C3CCOCC3)C=2N=1.Cl.[CH2:32]([C@@H:34]1[CH2:38][NH:37][CH2:36][C@H:35]1[C:39]1[NH:40][C:41](=[O:54])[C:42]2[CH:47]=[N:46][N:45]([CH:48]3[CH2:53][CH2:52][O:51][CH2:50][CH2:49]3)[C:43]=2[N:44]=1)[CH3:33].C([BH3-])#N.[Na+].[CH:59]([C:61]1[CH:62]=[C:63]([CH:66]=[CH:67][CH:68]=1)[C:64]#[N:65])=O>>[CH2:32]([C@H:34]1[C@H:35]([C:39]2[NH:40][C:41](=[O:54])[C:42]3[CH:47]=[N:46][N:45]([CH:48]4[CH2:49][CH2:50][O:51][CH2:52][CH2:53]4)[C:43]=3[N:44]=2)[CH2:36][N:37]([CH2:59][C:61]2[CH:62]=[C:63]([CH:66]=[CH:67][CH:68]=2)[C:64]#[N:65])[CH2:38]1)[CH3:33]

Participants

Reactant 4

HCID 90670m-Formylbenzonitrile

HCID 5003444Sodium cyanoborohydride

HCID 1358864606-((3S,4S)-4-Methyl-1-((2-methylpyrimidin-5-YL)methyl)pyrrolidin-3-YL)-1-(tetrahydro-2H-pyran-4-YL)-1,5-dihydro-4H-pyrazolo[3,4-D]pyrimidin-4-one

HCID 1363442016-[(3S,4S)-4-ethylpyrrolidin-3-yl]-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one hydrogen chloride

Product 1

HCID 135886519HCID 135886519, compound

Procedure

Following the procedure for the preparation of 6-{(3S,4S)-4-methyl-1-[(2-methylpyrimidin-5-yl)methyl]pyrrolidin-3-yl}-1-(tetrahydro-2H-pyran-4-yl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one but substituting 6-[(3S,4S)-4-ethylpyrrolidin-3-yl]-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one hydrogen chloride, sodium cyanoborohydride and 3-formylbenzonitrile provided the title compound. 400 MHz 1H NMR (CDCl3) δ 8.01 (s, 1H), 7.73-7.41 (m, 4H), 4.79 (m, 1H), 4.72 (s, 1H), 4.12-4.09 (m, 2H), 3.82-3.70 (m, 2H), 3.61-3.54 (m, 2H), 3.27 (t, J=8.3 Hz, 1H), 3.02-2.97 (m, 2H), 2.71-2.70 (m, 1H), 2.37-2.30 (m, 2H), 2.20-2.14 (m, 1H), 1.90-1.87 (m, 2H), 1.61-1.60 (m, 1H), 1.51-1.49 (m, 1H), 0.91 (t, J=7.5 Hz, 3H). MS: (M+H m/z 433.2).

Sources & evidence

ORD record: ord-d28f3c7479704231ad49615da09440c4
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07964607B2

Reaction notes

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