Formaldehyde → HCID 66711266, compound

HRID 1262165Notes

Reaction equation

HRID 1262165 reaction equation
C(O[C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[C:17]([O:24][CH3:25])[CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.COC1C=C(C=CC=1[N+]([O-])=O)OC1CCNCC1.FC(F)(F)C(O)=O.C=O.COC1C=C(C=CC=1[N+]([O-])=O)OC1CCN(C)CC1.COC1C=C(OC2CCN(C)CC2)C=CC=1N.CS([C:92]1[N:97]=[CH:96][C:95]2=[CH:98][CH:99]=[C:100]([C:101]3[CH:106]=[CH:105][CH:104]=[CH:103][C:102]=3[O:107][CH3:108])[N:94]2[N:93]=1)=O>>[CH3:25][O:24][C:17]1[CH:16]=[C:15]([O:14][CH:11]2[CH2:10][CH2:9][N:8]([CH3:6])[CH2:13][CH2:12]2)[CH:20]=[CH:19][C:18]=1[NH:21][C:92]1[N:97]=[CH:96][C:95]2=[CH:98][CH:99]=[C:100]([C:101]3[CH:106]=[CH:105][CH:104]=[CH:103][C:102]=3[O:107][CH3:108])[N:94]2[N:93]=1

Participants

8

Reactant 7

HCID 712FormaldehydeHCID 6422Trifluoroacetic acidHCID 49759211HCID 49759211, compoundHCID 552341692-Methoxy-4-[(1-methylpiperidin-4-yl)oxy]anilineHCID 574161554-(3-Methoxy-4-nitrophenoxy)-1-methylpiperidineHCID 58577221HCID 58577221, compoundHCID 667107912-Methanesulfinyl-7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazine

Product 1

HCID 66711266HCID 66711266, compoundYield 16.3%

Procedure

Following a procedure analogous to Example 45, 4-(3-Methoxy-4-nitro-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester (2.9 g) was converted to 4-(3-Methoxy-4-nitro-phenoxy)-piperidine as the trifluoroacetic acid salt (3.0 grams) which was converted, using a procedure analogous to 232a, with formaldehyde to 4-(3-Methoxy-4-nitro-phenoxy)-1-methyl-piperidine (76%), which was converted to 2-Methoxy-4-(1-methyl-piperidin-4-yloxy)-phenylamine (100%) using a procedure analogous to 251b, which was converted, using a 2-Methanesulfinyl-7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazine (100 mg, 0.36 mmol), to the title compound (27 mgs, 16%). H-NMR (CDCl3) δ 8.70 (s, 1H), 8.25 (d, J=10.7 Hz, 1H), 8.03 (d, J=10.7 Hz, 1H), 7.44 (t, J=9.2 Hz, 1H), 7.30 (s, 1H), 7.16-7.02 (m, 3H), 6.85-96.82 (m, 1H), 6.53 (s, 1H), 6.42 (d, J=10.4 Hz, 1H), 4.27 (Broad s, 1H), 3.89 (s, 3H), 3.86 (s, 3H), 2.75-2.69 (m, 2H), 2.33 (s, 3H), 2.33-2.26 (m, 2H), 2.04-1.98 (m, 2H), 1.90-1.81 (m, 2H); LC/MS (ESI+): 460 (M+H).

Sources & evidence

ORD record
ord-cc5a538c18134f50a716360fd4e1b7c8
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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