HCID 66623351, compound → HCID 178426750, compound

HRID 415007Notes

Reaction equation

HRID 415007 reaction equation
C1(O[C:8](=[NH:12])[NH:9][C:10]#[N:11])C=CC=CC=1.[NH2:13][CH2:14][C:15]#[C:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[N:23]=[CH:22][N:21]=[C:20]2[NH:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][C:35]2[CH:36]=[N:37][C:38]([CH3:41])=[CH:39][CH:40]=2)=[C:30]([CH3:42])[CH:29]=1>C(O)(C)C>[C:8]([NH:9][C:10]([NH:13][CH2:14][C:15]#[C:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[N:23]=[CH:22][N:21]=[C:20]2[NH:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][C:35]2[CH:36]=[N:37][C:38]([CH3:41])=[CH:39][CH:40]=2)=[C:30]([CH3:42])[CH:29]=1)=[NH:11])#[N:12]

Participants

4

Reactant 2

HCID 66623351HCID 66623351, compoundHCID 178512385HCID 178512385, compound

Product 1

HCID 178426750HCID 178426750, compoundYield 51.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 2-phenyl-N-cyano-isourea (50 mg, 0.31 mmol) and [6-(3-amino-prop-1-ynyl)-quinazolin-4-yl]-[3-methyl-4-(6-methyl-pyridin-3-yloxy)-phenyl]-amine (30 mg, 0.076 mmol) in isopropanol (3 mL) was heated at 85° C. in a sealed tube. The reaction was cooled to room temperature after 5 hours. Solvent was removed via rotovap. The residue was then purified by FCC to give the final product (18 mg, 51%) as a light yellow solid. MS ESI (+) m/z 463 (M+1) detected; 1H NMR (400 MHz, deuterated DMSO) □ 9.9 (s, 1H), 8.7 (s, 1H), 8.6 (s, 1H), 8.2 (s, 1H), 7.8 (m, 2H), 7.75 (m, 2H), 7.2 (m, 3H), 7.0 (m, 3H), 4.22 (m, 2H), 2.42 (s, 3H), 2.2 (s, 3H).

Workup

  1. temperatureThe reaction was cooled to room temperature after 5 hours
  2. customSolvent was removed via rotovap
  3. customThe residue was then purified by FCC

Sources & evidence

ORD record
ord-f95e207759854d1dabcb44207cedcb6b
Source dataset
uspto-grants-2012_01
Patent number
US08088766B2

Reaction notes

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