Hydrazine hydrate (1:1) → HCID 46216156, compound

HRID 2367271Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10](F)[CH:9]=2)[CH:5]=[C:4]([NH:17][CH:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:20][CH2:19]2)[N:3]=1.O.[NH2:28][NH2:29]>C(O)C>[NH2:13][C:12]1[C:11]2[C:10](=[CH:9][C:8]([C:6]3[N:7]=[C:2]([NH2:1])[N:3]=[C:4]([NH:17][CH:18]4[C:26]5[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=5)[CH2:20][CH2:19]4)[CH:5]=3)=[CH:15][CH:14]=2)[NH:29][N:28]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To 4-[2-amino-6-(2,3-dihydro-1H-inden-1-ylamino)-4-pyrimidinyl]-2-fluorobenzonitrile (500 mg, 1.45 mmol) in ethanol (2 mL) was added hydrazine monohydrate (3 mL, 74.0 mmol), and the reaction mixture was heated to 100° C. for 1 hour in a BiotageInitiator® microwave synthesizer. Upon cooling, the reaction mixture was concentrated in vacuum and purified by HPLC to afford the title compound (100 mg) as a brown solid. LC-MS (ES) m/z=358 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 1.81 (s, 1H), 1.90-1.92 (m, 1H), 2.84-3.051 (m, 2H), 5.43 (s, 2H), 5.71 (s, 1H), 6.12 (s, 2H), 6.40 (s, 1H), 7.23-7.48 (m, 6H), 7.75 (d, J=8.4 Hz, 1H), 7.90 (s, 1H), 11.58 (s, 1H).

Workup

temperatureUpon cooling
concentrationthe reaction mixture was concentrated in vacuum
custompurified by HPLC

Sources & evidence

ORD record: ord-e640b7dcb6b2478bbe9e64aefb4b5738
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697685B2

Reaction notes

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