Ammonium Acetate → HCID 178457875, compound

HRID 592035Notes

Reaction equation

[Cl:1][C:2]1[N:3]=[C:4]([N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[S:5][C:6]=1[CH:7]=O.[CH:14]([NH:17][C:18]([C@@H:20]1[C@H:25]([NH:26][C:27]2[C:32]([Cl:33])=[CH:31][N:30]=[C:29]([NH2:34])[C:28]=2[NH2:35])[C@@H:24]2[CH2:36][C@H:21]1[CH:22]=[CH:23]2)=[O:19])([CH3:16])[CH3:15].C([O-])(=O)C.[NH4+]>>[CH:14]([NH:17][C:18]([C@@H:20]1[C@H:25]([NH:26][C:27]2[C:32]([Cl:33])=[CH:31][N:30]=[C:29]3[NH:34][C:7]([C:6]4[S:5][C:4]([N:9]5[CH2:13][CH2:12][CH2:11][CH2:10]5)=[N:3][C:2]=4[Cl:1])=[N:35][C:28]=23)[C@@H:24]2[CH2:36][C@H:21]1[CH:22]=[CH:23]2)=[O:19])([CH3:16])[CH3:15]

Participants

Reactant 3

HCID 517165Ammonium Acetate

HCID 27630664-Chloro-2-(pyrrolidin-1-yl)-1,3-thiazole-5-carbaldehyde

HCID 117701981HCID 117701981, compound

Product 1

HCID 178457875HCID 178457875, compoundYield 3.4%

Procedure

In a similar fashion to Compound LXXXVII, 4-Chloro-2-pyrrolidin-1-yl-thiazole-5-carbaldehyde (69.84 mg, 0.3223 mmol), (1S,2S,3R,4R)-3-(2,3-Diamino-5-chloro-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid isopropylamide (97.42 mg, 0.2901 mmol), and Ammonium acetate (44.72 mg, 0.5802 mmol) were reacted to produce 5.21 mg (3.4%) of the title compound. (300 MHz, DMSO-d6) 12.60 (s, 1H), 8.10 (d, J=8 Hz, 1H), 7.93 (s, 1H), 6.90 (s, 1H), 6.34 (m, 2H), 5.00 (t, J=17 Hz, 8.5 Hz, 1H), 3.88 (m, 1H), 3.44 (m, 4H), 2.83 (s, 1H), 2.76 (s, 1H), 2.55 (d, J=8 Hz, 1H), 2.24 (d, J=8 Hz, 1H), 2.01 (m, 4H), 1.37 (d, J=8 Hz, 1H), 1.07 (d, J=7 Hz, 3H), 1.00 (d, J=7 Hz, 3H). MS=531 (M+H), HPLC: 3.11 min. (G Method)

Sources & evidence

ORD record: ord-18a6197524564936b8aabbc8c117a52d
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238656B2

Reaction notes

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