Formaldehyde → HCID 57955212, compound

HRID 73716Notes

Reaction equation

[NH2:1][C:2]1[C:7]2=[C:8]([C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20]([NH:22][C:23]4[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[CH:25][N:24]=4)=[O:21])=[CH:15][CH:14]=3)[C:9]([CH2:11][CH3:12])=[CH:10][N:6]2[N:5]=[CH:4][N:3]=1.[NH:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1.[CH2:39]=O>C(O)(=O)C.CCOC(C)=O>[NH2:1][C:2]1[C:7]2=[C:8]([C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20]([NH:22][C:23]4[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[CH:25][N:24]=4)=[O:21])=[CH:15][CH:14]=3)[C:9]([CH2:11][CH3:12])=[C:10]([CH2:39][N:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)[N:6]2[N:5]=[CH:4][N:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 1-[4-(4-amino-6-ethylpyrrolo[2,1-f][1,2,4]triazin-5-yl)phenyl]-3-[4-(trifluoromethyl)pyridin-2-yl]urea (120 mg, 0.7 mmol) in acetic acid (2 mL) was treated with a mixture of morpholine (240 μL, 2.72 mmol) and formaldehyde (37%, 204 μL, 2.72 mmol) in acetic acid (1 mL). The reaction was heated to 60° C. overnight. The reaction was then diluted with EtOAc and washed with NaHCO3. The organic layer was dried (MgSO4) and concentrated. The pale orange solid was then triturated with ether. The desired product was collected by vacuum filtration (30 mg, 20%). 1H-NMR (DMSO-d6) δ 9.95 (bs, 1H), 9.82 (bs, 1H), 8.55 (d, J=4.1 Hz, 1H), 8.07 (s, 1H), 7.86 (s, 1H), 7.64 (d, J=6.8 Hz, 2H), 7.38-7.32 (m, 3H), 3.82 (s, 2H), 3.53-3.50 (m, 4H), 2.54-2.49 (m, 2H), 2.44-2.41 (m, 4H), 0.97 (t, J=7.5 Hz, 3H). MS [M+H]+=541.1; LCMS RT=2.86.

Workup

washwashed with NaHCO3
dry with materialThe organic layer was dried (MgSO4)
concentrationconcentrated
customThe pale orange solid was then triturated with ether
filtrationThe desired product was collected by vacuum filtration (30 mg, 20%)
customLCMS RT=2.86

Sources & evidence

ORD record: ord-4340df212e884db7b0fcff01f1595284
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08829185B2

Reaction notes

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