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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1040723Generated: October 25, 2026

2-Bromopyridine → 5-Chloro-N*2*-[3-(2-methoxy-ethyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yl]-N*4*-(2-pyridin-2-yl-phenyl)-pyrimidine-2,4-diamine

https://huagongshe.com/reaction/1040723

Reaction equation

Participants

RoleNameHCIDCharge
Reactant2-BromopyridineHCID 7973—
Reactant2-Iodo-1-methyl-1H-imidazoleHCID 335835—
Reactant3-Ethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamineHCID 18943401—
Reactant3-(2-Methoxy-ethyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamine 5-Chloro-N*2*-[3-(2-methoxy-ethyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yl]-N*4*-(2-pyridin-2-yl-phenyl)-pyrimidine-2,4-diamineHCID 131730900—
Product5-Chloro-N*2*-[3-(2-methoxy-ethyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yl]-N*4*-(2-pyridin-2-yl-phenyl)-pyrimidine-2,4-diamineHCID 131730899—

Reaction Steps

Example 224 was synthesized analogously to Example 216 replacing 2-iodo-1-methyl-1H-imidazole with 2-bromopyridine and 3-Ethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamine with 3-(2-Methoxy-ethyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamine 5-Chloro-N*2*-[3-(2-methoxy-ethyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yl]-N*4*-(2-pyridin-2-yl-phenyl)-pyrimidine-2,4-diamine was isolated as a foam. (m+H)=503.02. 1H NMR (400 MHz, MeOD, d4) δ 8.97 (d, 2H, J=4.94 Hz), 8.76 (m, 1H), 8.60 (d, 1H, J=7.82 Hz), 8.13 (s, 1H), 7.56 (s, 1H), 7.45 (m, 3H), 7.28 (m, 2H), 7.21 (d, 1H, J=8.13 Hz), 3.79 (m, 4H), 3.51 (m, 2H), 3.47 (s, 3H), 3.25 (m, 2H), 3.15 (m, 4H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08552186B2
Source datasetuspto-grants-2013_10
ORD IDord-f3656d7b8d754300bbe8823dde9b3d9d
Source noteuspto-grants-2013_10