3-(Trifluoromethoxy)benzaldehyde → HCID 24937860, compound

HRID 391616Notes

Reaction equation

HRID 391616 reaction equation
FC(C1C=CC=CC=1N1C2NCNC=2C(C(N)=[O:21])=NC1)(F)F.[NH2:23]/[C:24](/[C:40]#[N:41])=[C:25](\[NH:28][C:29]([NH:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[O:38][CH3:39])=[O:30])/[C:26]#[N:27].[F:42][C:43]([F:54])([F:53])[O:44][C:45]1[CH:46]=[C:47]([CH:50]=[CH:51][CH:52]=1)[CH:48]=O>>[CH3:39][O:38][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=1[N:31]1[C:29](=[O:30])[NH:28][C:25]2[C:26]1=[N:27][C:48]([C:47]1[CH:50]=[CH:51][CH:52]=[C:45]([O:44][C:43]([F:42])([F:53])[F:54])[CH:46]=1)=[N:23][C:24]=2[C:40]([NH2:41])=[O:21]

Participants

4

Reactant 3

HCID 6051393-(Trifluoromethoxy)benzaldehydeHCID 57474547HCID 57474547, compoundHCID 178513821HCID 178513821, compound

Product 1

HCID 24937860HCID 24937860, compoundYield 22%

Procedure

9-(2-Methoxyphenyl)-8-oxo-2-(3-(trifluoromethylphenyl)-8,9-dihydro-7H-purine-6-carboxamide. (Z)-1-(2-Amino-1,2-dicyanovinyl)-3-(2-methoxyphenyl)urea (See Example 2.A) (0.50 g, 1.9 mmol) and 3-(trifluoromethoxy)benzaldehyde (0.52 g, 2.0 mmol) were reacted according to General Procedure B. The resultant heterogeneous mixture was filtered, and triturated with methanol/diethyl ether while sonicating. The brown solid, recovered by filtration, was triturated a second time using methanol/diethyl ether to afford a yellow powder that was subsequently dried under high vacuum at 60° C. to afford the title compound (0.19 g, 0.43 mmol, 22% yield). 1H NMR (400 MHz, DMSO-d6) δ 11.83 (s, 1H), 8.66 (s, 1H), 8.40 (s, 1H), 8.34 (d, J=8.2, 1H), 8.01 (s, 1H), 7.53-7.60 (m, 2H), 7.50 (dd, J=7.6, 1.4, 1H), 7.44 (d, J=8.2, 1H), 7.30 (d, J=8.2, 1H), 7.16 (t, J=7.4, 1H), 3.75 (s, 3H); MS (ESI) m/z 446.1 [M+1]+; mp 269-272° C.

Workup

  1. filtrationThe resultant heterogeneous mixture was filtered
  2. customtriturated with methanol/diethyl ether
  3. customwhile sonicating
  4. filtrationThe brown solid, recovered by filtration
  5. customwas triturated a second time
  6. customto afford a yellow powder that
  7. customwas subsequently dried under high vacuum at 60° C.

Sources & evidence

ORD record
ord-ab882db55e3743b983ede8894d278d37
Source dataset
uspto-grants-2013_02
Patent number
US08383634B2

Reaction notes

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