Ammonium Acetate → HCID 178480901, compound

HRID 592043Notes

Reaction equation

HRID 592043 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][O:10][C:11]2[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=2)[CH2:4][CH2:3]1.[CH3:19][N:20]([CH3:40])[C:21]([C@@H:23]1[C@H:28]([NH:29][C:30]2[C:35]([Cl:36])=[CH:34][N:33]=[C:32]([NH2:37])[C:31]=2[NH2:38])[C@@H:27]2[CH2:39][C@H:24]1[CH:25]=[CH:26]2)=[O:22].C([O-])(=O)C.[NH4+]>>[CH3:19][N:20]([CH3:40])[C:21]([C@@H:23]1[C@H:28]([NH:29][C:30]2[C:35]([Cl:36])=[CH:34][N:33]=[C:32]3[NH:37][C:15]([C:14]4[CH:17]=[CH:18][C:11]([O:10][CH2:9][CH2:8][N:5]5[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]5)=[CH:12][CH:13]=4)=[N:38][C:31]=23)[C@@H:27]2[CH2:39][C@H:24]1[CH:25]=[CH:26]2)=[O:22]

Participants

4

Reactant 3

HCID 517165Ammonium AcetateHCID 9769754-[2-(4-Methyl-piperazin-1-yl)-ethoxy]-benzaldehydeHCID 117701995HCID 117701995, compound

Product 1

HCID 178480901HCID 178480901, compoundYield 28.3%

Procedure

In a similar fashion to Compound LXXXVII, 4-(2-(4-methylpiperazin-1-yl)ethoxy)benzaldehyde (138 mg, 0.222 mmol), (1S,2S,3R,4R)-3-(2,3-Diamino-5-chloro-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid dimethylamide (78.7 mg, 0.244 mmol), and Ammonium acetate (34.3 mg, 0.444 mmol) were reacted to produce 34.61 mg (28%) of the title compound. (300 MHz, DMSO-d6) 12.56 (s, 1H), 8.08 (d, J=8 Hz, 1H), 7.93 (s, 1H), 7.88 (s, 1H), 7.11 (d, J=8 Hz, 1H), 6.42 (m, 2H), 6.32 (s, 1H), 5.35 (m, 1H), 4.15 (m, 2H), 3.49 (m, 1H), 3.07 (d, J=8 Hz, 1H), 3.00 (d, J=8 Hz, 1H), 2.96-2.68 (m, 14H), 2.32 (s, 2H), 2.14 (s, 2H), 1.92 (m, 1H), 1.44 (m, 1H). MS=550 (M+H), HPLC: 1.91 min. (G Method)

Sources & evidence

ORD record
ord-fcde3a7e3deb447fadba51ee08c2b588
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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