Formic Acid → HCID 86720055, compound

HRID 510132Notes

Reaction equation

N[C:2]1[N:10]=[C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[C:17]([F:20])[CH:18]=3)[N:13]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[F:28])[N:12]=2)[N:8]=[C:7]2[C:3]=1[N:4]([CH2:30][C:31]([F:34])([F:33])[F:32])[C:5](=[O:29])[NH:6]2.N(OCCC(C)C)=O.C(#N)C.O.C(O)=O.[I:50]CI>>[F:20][C:17]1[CH:18]=[C:19]2[C:11]([C:9]3[N:8]=[C:7]4[C:3]([N:4]([CH2:30][C:31]([F:33])([F:34])[F:32])[C:5](=[O:29])[NH:6]4)=[C:2]([I:50])[N:10]=3)=[N:12][N:13]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[F:28])[C:14]2=[N:15][CH:16]=1

Participants

Reactant 5

HCID 284Formic Acid

HCID 6346Diiodomethane

HCID 8053Isoamyl Nitrite

HCID 18373917Acetonitrile--water (1/1)

HCID 666135666-Amino-2-[5-fluoro-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-7-(2,2,2-trifluoroethyl)-7,9-dihydro-8H-purin-8-one

Product 1

HCID 86720055HCID 86720055, compound

Conditions

Temperature: 85 °C

Procedure

4.650 g (5.954 mmol) of the compound from example 62 were dissolved in 12 ml of diiodomethane and admixed with 12.76 ml (95.270 mmol) of isopentyl nitrite. The reaction mixture was heated to 85° C. for 16 h and, after cooling, concentrated on a rotary evaporator. 5 g of the crude product (purity 54%) were obtained. 1.2 g of the residue were by means of preparative HPLC (eluent: acetonitrile/water with 0.05% formic acid, gradient 40:60→95:5). 128 mg of the title compound were obtained (15% of theory).

Workup

temperatureafter cooling
concentrationconcentrated on a rotary evaporator
custom5 g of the crude product (purity 54%) were obtained

Sources & evidence

ORD record: ord-6d0ff7b89273487393f50ad8b28d2533
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096592B2

Reaction notes

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